2-Chlorophenothiazine → 2-chloro-10-(3-chloropropyl)-10H-phenothiazine

HRID 1078636Notes

Reaction equation

HRID 1078636 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22].C([N+](CCCC)(CCCC)CCCC)CCC>CC(C)CC(=O)C>[Cl:3][C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:19][CH2:20][CH2:21][Cl:22])[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 70882-ChlorophenothiazineHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 16028Tetrabutylammonium

Product 1

HCID 759982-chloro-10-(3-chloropropyl)-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

40 ml of a sodium hydroxide solution (50% by weight) are added to a solution of 2.34 g (10 mmol) of 2-chlorophenothiazine, 4.73 g (30 mmol) of 1-bromo-3-chloropropane and 0.34 g (1 mmol) of tetrabutylammonium hydrogenosulfate in 40 ml of 4-methylpentan-2-one. The mixture is stirred at ambient temperature for 48 hours. After customary treatment of the organic phase, drying over sodium sulfate, evaporation of the solvent and purification by chromatography on silica gel, 2.17 g of pure product are obtained (eluant: petroleum ether).

Workup

  1. dry with materialAfter customary treatment of the organic phase, drying over sodium sulfate, evaporation of the solvent and purification by chromatography on silica gel, 2.17 g of pure product
  2. customare obtained (eluant: petroleum ether)

Sources & evidence

ORD record
ord-c179d29058564ec8bd90428ec705188e
Source dataset
uspto-grants-1996_08
Patent number
US05550143

Reaction notes

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