Water → 2-Amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene

HRID 1834802Notes

Reaction equation

HRID 1834802 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]([O:16][CH3:17])=[O:15])=[S:12])=[C:6]([N+:18]([O-])=O)[CH:5]=1)[CH3:2].O>CO>[NH2:18][C:6]1[CH:5]=[C:4]([S:3][CH2:1][CH3:2])[CH:9]=[CH:8][C:7]=1[NH:10][C:11]([NH:13][C:14]([O:16][CH3:17])=[O:15])=[S:12]

Participants

4

Reactant 2

HCID 962WaterHCID 203720534-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene

Product 1

HCID 203720472-Amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzeneYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene (14.0 g), ferrous chloride tetrahydrate (3.04 g), methanol (235 ml) and water (50 ml) was heated to reflux and treated with reduced iron powder (15.5 g) portionwise during 5 minutes. The mixture was heated at reflux with stirring for one hour. Methanol (250 ml) was added and the mixture was again heated to reflux. The hot mixture was filtered and the filtrate was allowed to cool to room temperature. The solid which crystallised on cooling was filtered off to give 2-amino-4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)benzene (7.5 g), m.p. 168° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated
  4. temperatureat reflux
  5. temperaturethe mixture was again heated to reflux
  6. filtrationThe hot mixture was filtered
  7. customThe solid which crystallised
  8. temperatureon cooling
  9. filtrationwas filtered off

Sources & evidence

ORD record
ord-3a0aa6bb3e324aed984e0a419dfd9b8d
Source dataset
uspto-grants-1978_01
Patent number
US04071528

Reaction notes

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