Diethyl Ether → HCID 5257545, compound

HRID 1626255Notes

Reaction equation

HRID 1626255 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](OCC)C>>[CH3:16][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

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 70882-Chlorophenothiazine

Product 1

HCID 5257545HCID 5257545, compoundYield 37%

Procedure

To a solution of 2-chlorophenothiazine (4.67 g, 20 mmol) in anhydrous ethyl ether (60 mL) methyllithium (1.6 m solution, 62.5 mL, 0.1 mole) was added at room temperature (1 h). After that the mixture had been stirred (6 h), ice-water was added slowly, 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 (37% yield). Compound was purified by flash chromatography.

Workup

  1. additionwas added slowly
  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-3f4ae3a2bd9647d2a32cb4085b001a71
Source dataset
uspto-grants-2014_07
Patent number
US08785434B2

Reaction notes

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