HCID 9866247, compound → HCID 131721470, compound

HRID 1604277Notes

Reaction equation

HRID 1604277 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH2:10][CH:9]([CH3:16])[CH:8](C(OC(C)(C)C)=O)[C:7](=[O:24])[C:6]=1[S:5]2>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH2:10][CH:9]([CH3:16])[CH2:8][C:7](=[O:24])[C:6]=1[S:5]2

Participants

3

Reactant 1

HCID 9866247HCID 9866247, compound

Product 1

HCID 131721470HCID 131721470, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 7-bromo-3-carbo-ter-butoxy-2-methyl-2,3-dihydro-1H-phenothiazin-4[10H]-one (4l R=Br, 3.09 g, 13.7 mmole) in DMSO (10 mL) is placed in a preheated heating mantle. The reaction mixture is stirred and refluxed for 3 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 is separately recrystallized twice from MeOH and proves to be identical. An analytical sample of 4m, (R=Br), mp 250° (dec.) occurs as light orange crystals, 2.67 g (63.2%).

Workup

  1. temperaturerefluxed for 3 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 is separately recrystallized twice from MeOH

Sources & evidence

ORD record
ord-11689d3a8565433e8aa60791d8c172ed
Source dataset
uspto-grants-1999_11
Patent number
US05994349

Reaction notes

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