4-Mercaptophenol → 2-nitro-4-amino-5-(parahydroxyphenyl)thio-N-(methyl)aniline

HRID 363816Notes

Reaction equation

[N+:1]([C:4]1[CH:11]=[C:10]([NH2:12])[C:9](Cl)=[CH:8][C:5]=1[NH:6][CH3:7])([O-:3])=[O:2].[SH:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>>[N+:1]([C:4]1[CH:11]=[C:10]([NH2:12])[C:9]([S:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:8][C:5]=1[NH:6][CH3:7])([O-:3])=[O:2]

Participants

Reactant 2

HCID 2401474-Mercaptophenol

HCID 537934652-nitro-4-amino-5-chloro-N-(methyl)aniline

Product 1

HCID 152951732-nitro-4-amino-5-(parahydroxyphenyl)thio-N-(methyl)anilineYield 68%

Procedure

11.5 g (0.057 mol) of 2-nitro-4-amino-5-chloro-N-(methyl)aniline and 11.9 g (0.085 mol) of 4-mercaptophenol were used as the starting materials to give brown-orange crystals (11.3 g) recrystallized from 96° ethanol and melting at 206° C., whose elemental analysis calculated for C13H13N3O3S was:

Sources & evidence

ORD record: ord-ff861c1e3001466bbba3d7a13732463a
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05874618

Reaction notes

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