Methoxycarbonyl isothiocyanate → HCID 20371047, compound

HRID 616104Notes

Reaction equation

HRID 616104 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[NH2:16].[CH3:17][O:18][C:19]([N:21]=[C:22]=[S:23])=[O:20]>CC(C)=O>[CH3:17][O:18][C:19]([NH:21][C:22](=[S:23])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[NH:16][C:22]([NH:21][C:19]([O:18][CH3:17])=[O:20])=[S:23])=[O:20]

Participants

4

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 10657374HCID 10657374, compound

Product 1

HCID 20371047HCID 20371047, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.2 G. of 2-amino-4-(4-chlorophenoxy)-1-nitrobenzene in 3ml. concentrated hydrochloric acid is treated with a solution of 6 g. stannous chloride in 3 ml. concentrated hydrochloric acid. The mixture is heated briefly (about ten minutes) on a steam bath, then cooled and treated with potassium bicarbonate and chloroform. The chloroform layer is removed from the filtered mixture, dried and evaporated. 1,2-diamino-4-(4-chlorophenoxy)benzene is isolated as a gum. 1G. of 1,2-diamino-4-(4-chlorophenoxy)benzene in 20 ml. acetone is treated overnight at room temperature with 2.5 g. methoxy carbonyl isothiocyanate. The mixture is concentrated under vacuum and the residue triturated with methanol. Recrystallization from methanol gives pure 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-(4-chlorophenoxy)benzene.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customthe residue triturated with methanol
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-a056454850c14316a1c4cc3cd990bf18
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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