Methoxycarbonyl isothiocyanate → HCID 20371044, compound

HRID 616119Notes

Reaction equation

HRID 616119 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:10][CH:11]=[CH2:12])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:25][C:26]#[CH:27])=[O:24])=[CH:19][C:18]=1[N+:28]([O-:30])=[O:29].[CH3:31][O:32][C:33]([N:35]=[C:36]=[S:37])=[O:34]>CC(C)=O>[CH3:31][O:32][C:33]([NH:35][C:36](=[S:37])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:10][CH:11]=[CH2:12])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])=[O:34].[CH3:31][O:32][C:33]([NH:35][C:36](=[S:37])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:25][C:26]#[CH:27])=[O:24])=[CH:19][C:18]=1[N+:28]([O-:30])=[O:29])=[O:34]

Participants

6

Reactant 3

HCID 552246Methoxycarbonyl isothiocyanateHCID 203710631-Amino-2-nitro-4-(prop-2-en-1-ylsulfinyl)-benzeneHCID 20371138HCID 20371138, compound

Product 2

HCID 20371044HCID 20371044, compoundHCID 20371128HCID 20371128, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.5 G. of 1-amino-2-nitro-4-(prop-2-en-1-ylsulfinyl)-benzene or 1-amino-2-nitro-4-(prop-2-yn-1-ylsulfinyl)benzene, prepared according to Example XXII, in 200 ml. acetone is treated with 4 g. methoxy carbonyl isothiocyanate at room temperature for several days (i.e., until no starting material is present). The mixture is concentrated and the residue triturated with methanol to yield 1-(3-methoxycarbonyl-2-thioureido)-2-nitro-4-(prop-2-en-1-ylsulfinyl)benzene or 1-(3-methoxycarbonyl-2-thioureido)-2-nitro-4-(prop-2-yn-sulfinyl)benzene, respectively.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue triturated with methanol

Sources & evidence

ORD record
ord-42e102eca30f42c9964c062554572626
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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