Methanethiol → 3-(Methylsulfanyl)-4-nitroaniline

HRID 1732864Notes

Reaction equation

HRID 1732864 reaction equation
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:12][SH:13].Cl[C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[NH2:18]>O>[CH3:12][S:13][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[NH2:18]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699963-Chloro-4-nitroaniline

Product 1

HCID 130256833-(Methylsulfanyl)-4-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of dry dimethylformamide (150 ml) and potassium carbonate (12.0 g) is stirred and methyl mercaptan is introduced as a gas for 45 minutes. After stirring for another 45 minutes, 3-chloro-4-nitroaniline (10.0 g) is added. The mixture is stirred and heated at 120°-130° C. for 18 hours. It is then cooled and poured into water (1 liter), the precipitate is collected and recrystallized from methanol to afford 8 grams of 3-methylthio-4-nitroaniline, m.p. 178°-182° C.

Workup

  1. stirringAfter stirring for another 45 minutes
  2. stirringThe mixture is stirred
  3. temperatureheated at 120°-130° C. for 18 hours
  4. temperatureIt is then cooled
  5. customthe precipitate is collected
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d9495587579d4558b1ab5540807ecc27
Source dataset
uspto-grants-1980_12
Patent number
US04239708

Reaction notes

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