Benzyl mercaptan → HCID 53730043, compound

HRID 2106944Notes

Reaction equation

HRID 2106944 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22]([Br:24])[CH:21]=[C:20]([N+:25]([O-:27])=[O:26])[C:19]=1Cl>CO.O>[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22]([Br:24])[CH:21]=[C:20]([N+:25]([O-:27])=[O:26])[C:19]=1[S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 43449021HCID 43449021, compound

Product 1

HCID 53730043HCID 53730043, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
20 °C

Procedure

71.6 g (0.58 mol) of benzyl mercaptan are dissolved in 2.9 l of methanol/water (8:2), and 79.8 g (0.58 mol) of potassium carbonate are added. At 0°-5° C., 170 g (0.58 mol) of 5-bromo-2-chloro-3-nitrobenzoic acid methyl ester are added in portions over a period of 2.5 hours with stirring. Stirring is then continued for a further 2 hours and the internal temperature is then raised to 20° C. The resulting precipitate is then isolated by filtration, washed with a small amount of water and subsequently with 500 ml of methanol/water. After drying, 208 g (94%) of pale yellow product are obtained. Recrystallisation from 400 ml of methanol gives 190 g (86% of the theoretical yield) of product having a melting point of 65°-66° C.

Workup

  1. stirringStirring
  2. customThe resulting precipitate is then isolated by filtration
  3. washwashed with a small amount of water and subsequently with 500 ml of methanol/water
  4. customAfter drying

Sources & evidence

ORD record
ord-b5769287d7fe45e2bec5a33d91e6763a
Source dataset
uspto-grants-1990_06
Patent number
US04931581

Reaction notes

Loading…