Water → HCID 20376738, compound

HRID 1862993Notes

Reaction equation

HRID 1862993 reaction equation
[Na].[CH2:2]([SH:4])[CH3:3].CC([NH:8][C:9]1[CH:14]=[C:13](Cl)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])=O.O>COCCO>[CH2:2]([S:4][C:13]1[CH:12]=[CH:11][C:10]([N+:16]([O-:18])=[O:17])=[C:9]([CH:14]=1)[NH2:8])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 224170n-(5-chloro-2-nitrophenyl)acetamideHCID 5360545Sodium

Product 1

HCID 20376738HCID 20376738, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent3×

Conditions

Temperature
10 °C

Procedure

Sodium (2.76 g.) was added to dry 2-methoxyethanol (75 ml.) and the solution was cooled to 0°-5° C. Ethanethiol (8.72 g.) in 2-methoxyethanol (10 ml.) was added during 5 minutes and the subsequent solution was stirred at 0°-5° C. for 10 minutes and then added in portions to a solution of 5-chloro-2-nitro acetanilide (21.5 g.) in boiling 2-methoxyethanol (150 ml.) during 10 minutes. After 3 hours the mixture was cooled and poured into water (1 l.). The mixture was stirred and cooled to 10° C. The solid which formed was collected by filtration, washed with water, and recrystallized from ethanol to give 5-ethylthio-2-nitroaniline (16.4 g.), m.p. 75°-6° C.

Workup

  1. temperaturethe solution was cooled to 0°-5° C
  2. customduring 10 minutes
  3. temperatureAfter 3 hours the mixture was cooled
  4. stirringThe mixture was stirred
  5. customThe solid which formed
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-120d65162ba6414bbf528ea7205be194
Source dataset
uspto-grants-1979_09
Patent number
US04167569

Reaction notes

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