Phenaglycodol (brand names Acalmid, Acalo, Alterton, Atadiol, Felixyn, Neotran, Pausital, Remin, Sedapsin, Sinforil, Stesil, Ultran) is a

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

described as a tranquilizer or

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but t ...

which has anxiolytic and

anticonvulsant Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of b ...

properties. It is related

pharmacologically Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemica ...

to meprobamate, though it is not a

carbamate In organic chemistry, a carbamate is a category of organic compounds with the general formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally o ...

Synthesis

''p''-Chloroacetophenone and NaCN are reacted together to give the corresponding

cyanohydrin In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is , where R is H, alkyl, or aryl. Cyanohydrin ...

(cf Strecker synthesis)
CID:12439573
The cyano group is then hydrated in acid to the corresponding amide, ''p''-chloroatrolactamide
CID:15255544
(4). The amide group is then further hydrolyzed with a 2nd equivalent of water in concentrated lye to ''p''-chloroatrolactic acid, 445-13-0(5). Esterification to Ethyl ''p''-chloroatrolactate 00126-96-36). Finally,

nucleophilic addition In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions di ...

a couple of equivalents of MeMgI are added to the ester give Phenaglycodol (7) crystals. Phenaglycodol synthesis2

A mixed

Pinacol coupling A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process. The reaction product is a vicinal diol. ...

rxn between 4-chloroacetophenone 9-91-2and

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

with magnesium activated with a small amount of trimethylsilyl chloride gave a 40% yield of phenglycodol.

Notes

*See "Novel trifluoromethyl derivatives of substituted diols" also. *A Pinacol rearrangement occurs in acidic water:Murphy, Hubert W. (1964). "Pinacol Rearrangement of Phenaglycodol I". Journal of Pharmaceutical Sciences. 53 (3): 298–301. doi:10.1002/jps.2600530311.

References

Anticonvulsants Anxiolytics Sedatives {{sedative-stub

Synthesis

Notes

See also

References