Methoxycarbonyl isothiocyanate → 1-(3-Methoxycarbonyl-2-thioureido)-2-nitro-4-methoxymethylthiobenzene

HRID 616122Notes

Reaction equation

HRID 616122 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][O:10][CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][O:16][C:17]([N:19]=[C:20]=[S:21])=[O:18]>CC(C)=O>[CH3:15][O:16][C:17]([NH:19][C:20](=[S:21])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][O:10][CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])=[O:18]

Participants

4

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 203628174-[(Methoxymethyl)sulfanyl]-2-nitroaniline

Product 1

HCID 203711251-(3-Methoxycarbonyl-2-thioureido)-2-nitro-4-methoxymethylthiobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1 G. of 1-amino-2-nitro-4-methoxymethylthiobenzene, prepared according to Example VIII, in 50 ml. acetone is treated with 3 g. methoxy carbonyl isothiocyanate at room temperature for several days. The solution is concentrated and the residue triturated with methanol and recrystallized from acetone to afford 1-(3-methoxycarbonyl-2-thioureido)-2-nitro-4-methoxymethylthiobenzene. This latter compound is treated for four hours in a refluxing mixture of 160 ml. methanol and 40 ml. water with 4 g. iron powder (added in two portions) and 1 g. ferrous sulfate. The mixture is filtered, and the filtrate concentrated. The residue is dissolved in chloroform, washed with water, then the solvent is evaporated to afford 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-methoxymethylthiobenzene.

Workup

  1. concentrationThe solution is concentrated
  2. customthe residue triturated with methanol
  3. customrecrystallized from acetone

Sources & evidence

ORD record
ord-ddaf654ba5614c5697cbfbd59cc8746c
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

Loading…