Water → 1-Amino-4-ethylthio-2-nitrobenzene

HRID 258763Notes

Reaction equation

HRID 258763 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+].[CH2:16](I)C.O>C(O)C>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([S:11][CH2:12][CH3:16])=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 1046774-Amino-3-nitrophenyl thiocyanate

Product 1

HCID 203720451-Amino-4-ethylthio-2-nitrobenzeneYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitro-4-thiocyanatoaniline (17.55 g.; prepared as hereinbefore described in Example 6) was added portionwise to a stirred solution of potassium hydroxide (13.4 g.) in ethanol (210 ml.), keeping the temperature below 20° C. After 5 minutes, ethyl iodide (14.4 g.) was added during five minutes. The stirring was continued for a further hour and the mixture was allowed to stand overnight. The mixture was then poured into water (1100 ml.) and extracted with chloroform (3× 300 ml.). The chloroform layers were combined, washed with water (500 ml.), dried over magnesium sulphate, and evaporated to give 1-amino-4-ethylthio-2-nitrobenzene (17.0 g.), in the form of a red oil.

Workup

  1. customthe temperature below 20° C
  2. waitThe stirring was continued for a further hour
  3. waitto stand overnight
  4. extractionextracted with chloroform (3× 300 ml.)
  5. washwashed with water (500 ml.)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-cf7be3f1627b4665a1d58e057e9d82a1
Source dataset
uspto-grants-1977_07
Patent number
US04034107

Reaction notes

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