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

HRID 979086Notes

Reaction equation

HRID 979086 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 g) 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-208036c4c3594019a519dcf55deb033f
Source dataset
uspto-grants-1987_05
Patent number
US04666907

Reaction notes

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