Benzyl mercaptan → HCID 19384363, compound

HRID 2399697Notes

Reaction equation

HRID 2399697 reaction equation
Cl[C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11]([SH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:11]([S:18][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 5933762-Chloro-3-hydroxybenzaldehyde

Product 1

HCID 19384363HCID 19384363, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

174 g of 2-chloro-3-hydroxybenzaldehyde are dissolved in 1 l of dimethylformamide, 126 ml of benzylmercaptan and 174 g of potassium carbonate are added, and the mixture is stirred for 2 days at 100° C. The reaction mixture is poured into ice-water and extracted using diethyl ether, and the organic phase is washed with saline, dried over sodium sulfate, filtered and concentrated. Silica gel chromatography with ethyl acetate/hexane (1:4) as the mobile phase gives 51.6 g of 2-benzylthio-3-hydroxybenzaldehyde. 31.6 g of this are emulsified in 66 ml of water, and 16.1 g of hydroxylamine-O-sulfonic acid and 1.84 g of sodium sulfate are added. After one hour, 32 ml of each water and methylene chloride are added, and the mixture is treated with 40.4 g of sodium hydrogen carbonate in portions. The reaction mixture is stirred for 2 hours at room temperature and then taken up in methylene chloride, and the organic phase is extracted using 1N potassium hydroxide solution. The aqueous-basic phase is brought to a pH of 1 using concentrated hydrochloric acid and extracted using methylene chloride. The organic phase is dried over sodium sulfate, filtered and concentrated. Recrystallisation from toluene gives 5.93 g of 7-hydroxy-1,2-benzisothiazole of m.p. 185°-187° C.

Workup

  1. extractionextracted
  2. washthe organic phase is washed with saline
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3972c22d5f4b42759524d75970f0c816
Source dataset
uspto-grants-1995_09
Patent number
US05451595

Reaction notes

Loading…