Hydrogen Bromide → 2-Benzhydrylsulfanylacetic acid

HRID 457255Notes

Reaction equation

HRID 457255 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]([S+:14]([O-])[CH2:15][C:16](N)=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:6]=1.C1(C(C2C=CC=CC=2)[OH:27])C=CC=CC=1.NC(N)=S.Br.ClCC(O)=O>>[C:4]1([CH:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[S:14][CH2:15][C:16]([OH:17])=[O:27])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 260Hydrogen BromideHCID 300Chloroacetic AcidHCID 7037BenzhydrolHCID 2723790ThioureaHCID 178514057HCID 178514057, compound

Product 1

HCID 20778862-Benzhydrylsulfanylacetic acid

Procedure

Scheme 2 describes an industrial method for the preparation of Modafinil (II) wherein the all the reaction steps may be carried out in situ. In this scheme, the starting material is diphenylmethanol which is reacted with thiourea in the presence of HBr followed by basic hydrolysis and reaction with chloroacetic acid to form compound III. Hydrogen peroxide is then passed through the reaction mixture followed by acidification with hydrochloric acid to form (benzhydrylsulfinyl)acetic acid. The acid is reacted with dimethyl sulphate in presence of soda lye and sodium bicarbonate to obtain methyl(benzhydrylsulfinyl)acetate. After filtration methyl(benzhydrylsulfinyl)acetate is dissolved in methanol and ammonia is bubbled through the reaction mixture. After recrystallization and drying of the reaction mass Modafinil (II) is obtained with 41% total yield calculated from benzhydrol. The in-situ reaction scheme 2 is set out below.

Workup

  1. customthe reaction steps

Sources & evidence

ORD record
ord-646e587991464b47b0352df6db32aae1
Source dataset
uspto-grants-2007_03
Patent number
US07186860B2

Reaction notes

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