2-Aminothiophenol → 2-Methyl-2,3-dihydro-1H-phenothiazin-4(10H)-one

HRID 1604274Notes

Reaction equation

HRID 1604274 reaction equation
[CH3:1][CH:2]1[CH:7](C(OCCCC)=O)[C:6](=O)[CH2:5][C:4](=[O:16])[CH2:3]1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24]>CS(C)=O>[CH3:1][CH:2]1[CH2:3][C:4](=[O:16])[C:5]2[S:24][C:19]3[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:17][C:6]=2[CH2:7]1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 19602601HCID 19602601, compound

Product 1

HCID 156215282-Methyl-2,3-dihydro-1H-phenothiazin-4(10H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of ter butyl 6-methyl-2,4-dioxocyclohexane-1-carboxylate, 7c (3.09 g, 13.7 mmole) and 2-aminothiophenol, 6 (X=H, 1.71 g, 13.7 mmole) in DMSO (10 mL) is placed in a preheated heating mantle. The reaction mixture is stirred and refluxed for 0.5 h. Upon cooling, the reaction mixture forms a solid. The crystals are filtered and the remaining mother liquid is poured into cold water, whereupon further precipitation occurs. Each precipitate was separately recrystallized twice from MeOH and proves to be identical. An analytical sample of 4d, (R=H), mp 278° C. occurs as light orange crystals; yield: 0.46 g (15.4%).

Workup

  1. temperaturerefluxed for 0.5 h
  2. temperatureUpon cooling
  3. filtrationThe crystals are filtered
  4. additionthe remaining mother liquid is poured into cold water, whereupon further precipitation
  5. customEach precipitate was separately recrystallized twice from MeOH

Sources & evidence

ORD record
ord-c53f69dc79354be285c8875f7892502c
Source dataset
uspto-grants-1999_11
Patent number
US05994349

Reaction notes

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