Hydrochloric Acid → 2-Benzylthio-3-nitrobenzoic acid

HRID 2106953

Reaction equation

HRID 2106953 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+].[N+]([C:18]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])([O-])=O.Cl>CN(C)C=O>[CH2:1]([S:8][C:18]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 2833272,3-Dinitrobenzoic acid

Product 1

HCID 110553562-Benzylthio-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6.85 g (0.055 mol) of benzyl mercaptan are dissolved in 150 ml of dimethylformamide. The batch is then cooled to 0° C. and 15.2 g (0.11 mol) of potassium carbonate are added. 10.6 g (0.050 mol) of 2,3-dinitrobenzoic acid are then added in portions at from 0° to 5° C. and the internal temperature is afterwards raised to room temperature over a period of 24 hours. The reaction mixture is then poured onto ice/water and acidified with hydrochloric acid. The resulting product is filtered, washed with water and dried. Yield: 11.8 g (82% of the theoretical yield); m.p. 152°-153° C.

Workup

  1. temperaturethe internal temperature is afterwards raised to room temperature over a period of 24 hours
  2. additionThe reaction mixture is then poured onto ice/water
  3. filtrationThe resulting product is filtered
  4. washwashed with water
  5. customdried
  6. customYield: 11.8 g (82% of the theoretical yield)

Sources & evidence

ORD record
ord-52e9119d07684d02bda11a830016acc0
Source dataset
uspto-grants-1990_06
Patent number
US04931581

Linked notes

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