Methoxycarbonyl isothiocyanate → 1-(3-Methoxycarbonyl-2-thioureido)-4-methylthiomethoxy-2-nitrobenzene

HRID 616129Notes

Reaction equation

HRID 616129 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][S: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]>>[CH3:15][O:16][C:17]([NH:19][C:20](=[S:21])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][S:10][CH3:11])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])=[O:18]

Participants

3

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 203628264-[(Methylsulfanyl)methoxy]-2-nitroaniline

Product 1

HCID 203712191-(3-Methoxycarbonyl-2-thioureido)-4-methylthiomethoxy-2-nitrobenzene

Procedure

1-Amino-4-methylthiomethoxy-2-nitrobenzene, prepared according to Example XV, is treated with 3.0 g. methoxy carbonyl isothiocyanate at room temperature for nine days. The solution is concentrated and the residue triturated with ether and recrystallized to afford 1-(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxy-2-nitrobenzene. This latter compound is treated in accordance with the iron reduction technique set forth in the third paragraph of Example XIX to afford 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxybenzene. This latter compound is treated in accordance with the first paragraph of Example XVI to afford 2-acetamido-1-(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxybenzene.

Workup

  1. additionis treated with 3.0 g
  2. concentrationThe solution is concentrated
  3. customthe residue triturated with ether
  4. customrecrystallized

Sources & evidence

ORD record
ord-84e1001dbe224cf8b0a0d97284d724e5
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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