Diethyl Ether → HCID 5257545, compound

HRID 2405686Notes

Reaction equation

HRID 2405686 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, 0.020 mole) in anhydrous ethyl ether (60 mL) methyl lithium (R═CH3 in product) (1.6 M solution, 62.5 mL, 0.1 mol) was added at room temperature (1 h). After the mixture had been stirred for 6 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 (1.58 g, 37% yield). The desired final product was purified by flash chromatography.

Workup

  1. waitafter that the stirring was continued for 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-7dab93bafa364dc8bd261eb642723d27
Source dataset
uspto-grants-2014_08
Patent number
US08809317B2

Reaction notes

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