2-Aminothiophenol → 2,4-di-t-butyl-1-hydroxy-10H-phenothiazine

HRID 231052Notes

Reaction equation

HRID 231052 reaction equation
[C:1]([C:5]1[C:6](=[O:16])[C:7](=O)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24]>CO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]2[S:24][C:19]3[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:17][C:7]=2[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 769153,5-Di-tert-butyl-1,2-benzoquinone

Product 1

HCID 138820352,4-di-t-butyl-1-hydroxy-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-di-t-butyl-1,2-benzoquinone (2.2 q) in methanol (15 ml) cooled in an ice bath was added 2-aminothiophenol (1.38 g) and the mixture was stirred for 2 hours. A solid precipitate was filtered off and crystallized from heptane to yield the title compound m.p. 202°-212° (dec.). From the methanol filtrate there was obtained, after chromatography and crystallization, an additional crop of the title compound.

Workup

  1. filtrationA solid precipitate was filtered off
  2. customcrystallized from heptane

Sources & evidence

ORD record
ord-03b6e877bf1b4ebcb605976dc3437dd0
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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