1-Mercapto-2-propanol → 4-(2-Hydroxypropylthio)-2-methylbenzonitrile

HRID 923070Notes

Reaction equation

HRID 923070 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[SH:11][CH2:12][CH:13]([OH:15])[CH3:14]>>[OH:15][CH:13]([CH3:14])[CH2:12][S:11][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1

Participants

3

Reactant 2

HCID 1025451-Mercapto-2-propanolHCID 1442674-Bromo-2-methylbenzonitrile

Product 1

HCID 668773644-(2-Hydroxypropylthio)-2-methylbenzonitrile

Procedure

2 g of 4-bromo-2-methylbenzonitrile was reacted with 1-mercapto-2-propanol via Procedure Q to afford 4-(2-hydroxypropylthio)-2-methylbenzonitrile. 950 mg of 4-(2-hydroxypropylthio)-2-methylbenzonitrile was reacted via Procedure T to give 4-(2-hydroxypropylthio)-2-methylbenzoic acid. 1.0 g of 4-(2-hydroxypropylthio)-2-methylbenzoic acid was reacted via Procedure R to give 4-(2-hydroxypropylsulfonyl)-2-methylbenzoic acid. 100 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-(2-hydroxypropylsulfonyl)-2-methylbenzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(2-hydroxypropylsulfonyl)-2-methylbenzamide. MS (Q1) 445.3 (M)+.

Sources & evidence

ORD record
ord-8cf932fe33a64738bb9a564f8460bf9f
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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