2-Chlorophenothiazine → 1-propan-2-yl-10H-phenothiazine

HRID 1626258Notes

Reaction equation

HRID 1626258 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[CH2:16]1[CH2:20]OC[CH2:17]1>>[CH:16]([C:3]1[C:4]2[NH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[S:12][C:13]=2[CH:14]=[CH:15][CH:2]=1)([CH3:20])[CH3:17]

Participants

3

Reactant 2

HCID 70882-ChlorophenothiazineHCID 8028Tetrahydrofuran

Product 1

HCID 52575471-propan-2-yl-10H-phenothiazineYield 52%

Procedure

To a solution of 2-chlorophenothiazine (4.67 g, 20 mmol) in anhydrous THF (40 mL) i-propyllithium (0.7 m solution in pentane, 100 mL, 70 mmol) was added at −75° C. (1 h). The reaction mixture had been stirred (2 h), ice-water was added slowly (30 min.) and after that the stirring was continued for 30 min. The organic layer was separated and combined with ether extracts of the aqueous phase. The combined organic phase was washed with water, dried (Na2SO4) and concentrated to give the crude product (52% yield). Compound was purified by flash chromatography (solvent system: hexane-ethyl acetate).

Workup

  1. additionwas added slowly (30 min.)
  2. customThe organic layer was separated
  3. washThe combined organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2e34f53d44744047aece2e8b185e5292
Source dataset
uspto-grants-2014_07
Patent number
US08785434B2

Reaction notes

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