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

HRID 616143Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[CH3:21][O:22][C:23]([N:25]=[C:26]=[S:27])=[O:24]>>[CH3:21][O:22][C:23]([NH:25][C:26](=[S:27])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])=[O:24]

Participants

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanate

HCID 205454564-(2-Phenoxyethoxy)-2-nitroaniline

Product 1

HCID 203710371-(3-Methoxycarbonyl-2-thioureido)-2-nitro-4-(2-phenoxyethoxy)benzene

Procedure

The 1-amino-2-nitro-4-(2-phenoxyethoxy)benzene so obtained is treated with methoxycarbonyl isothiocyanate (as per Example XL) to afford 1-(3-methoxycarbonyl-2-thioureido)-2-nitro-4-(2-phenoxyethoxy)benzene which is reduced with sodium hydrosulfite (as per Example XXI) or iron-ferrous sulfate (as per Example VII) to afford 1-(3-methoxycarbonyl-2-thioureido)-2-amino-4-(2-phenoxyethoxy)benzene. The latter compound is further reacted with another equivalent of methoxycarbonyl isothiocyanate to afford 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-(2-phenoxyethoxy)benzene.

Sources & evidence

ORD record: ord-386d08404b164025aa59b27429156204
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04072696

Reaction notes

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