Hydrogen Bromide → 2-Benzhydrylsulfanylacetic acid

HRID 1828367Notes

Reaction equation

[CH:1](O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C:16](N)=[S:17].ClC[C:21]([OH:23])=[O:22].Br>>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:17][CH2:16][C:21]([OH:23])=[O:22])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 260Hydrogen Bromide

HCID 300Chloroacetic Acid

HCID 7037Benzhydrol

HCID 2723790Thiourea

Product 1

HCID 20778862-Benzhydrylsulfanylacetic acid

Procedure

U.S. Pat. No. 4,177,290 discloses an alternative process for the application on an industrial scale (scheme 2). Benzhydrol (5), thiourea (6) and 2-chloroacetic acid (7) are reacted in the presence of hydrobromic acid to obtain 2-[(diphenylmethyl)sulfenyl]acetic acid (8), which is oxidized with hydrogen peroxide to afford 2-[2-[(diphenylmethyl)sulfinyl]acetic acid (9). This is reacted with NaHCO3 and dimethyl sulfate and the resulting methyl ester (10) is converted to modafinil by treatment with ammonia.

Sources & evidence

ORD record: ord-1e9baba283b84f4e99d3f3786920a6b8
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07057068B2

Reaction notes

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