Water → 4-(Methylsulfanyl)-2-nitroaniline

HRID 258758Notes

Reaction equation

HRID 258758 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][C:12]#N)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[OH-].[K+].CI.O>C(O)C>[CH3:12][S:11][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 1046774-Amino-3-nitrophenyl thiocyanate

Product 1

HCID 108886074-(Methylsulfanyl)-2-nitroanilineYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitro-4-thiocyanato-aniline (17.6 g.) was added portionwise to a stirred solution of potassium hydroxide (13.4 g.) in ethanol (210 ml.) cooled below 15° C. After 5 minutes, methyl iodide (12.8 g.) was added to the purple solution and the mixture was allowed to stand overnight at room temperature. The mixture was then poured into water (1100 ml.) and the deep red solid was filtered off, washed with water, and dried to give 4-methylthio-2-nitroaniline (15.8 g.), m.p. 72°-73° C.

Workup

  1. temperaturecooled below 15° C
  2. waitto stand overnight at room temperature
  3. filtrationthe deep red solid was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5f1d566e205e4d2797ad974e92ce3565
Source dataset
uspto-grants-1977_07
Patent number
US04034107

Reaction notes

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