Methoxycarbonyl isothiocyanate → 4-n-Butylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene

HRID 616090Notes

Reaction equation

HRID 616090 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH3:16][O:17][C:18]([N:20]=[C:21]=[S:22])=[O:19]>CC(C)=O>[CH2:9]([S:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:21]([NH:20][C:18]([O:17][CH3:16])=[O:19])=[S:22])=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=1)[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 110315614-(Butylsulfanyl)-2-nitroaniline

Product 1

HCID 203710544-n-Butylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.5 G. of 1-amino-4-n-butylthio-2-nitrobenzene (alternatively prepared according to Example II) is dissolved in 25 ml. acetone and treated at room temperature with 3 g. methoxy carbonyl isothiocyanate. The mixture is left overnight, stripped under vacuum and the residue triturated with methanol and recrystallized from methanol to yield pure 4-n-butylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene.

Workup

  1. dissolutionis dissolved in 25 ml
  2. customthe residue triturated with methanol
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0878a5a5fd5b4eec8345d997b702a243
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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