Phenothiazine → 10-(3-chloropropyl)-10H-phenothiazine

HRID 1378415Notes

Reaction equation

HRID 1378415 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][Cl:21].[Cl-].[NH4+]>CN(C)C=O>[Cl:21][CH2:20][CH2:19][CH2:18][N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 7108PhenothiazineHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 1229912010-(3-chloropropyl)-10H-phenothiazineYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenothiazine (4.0 g, 0.02 mol) in dry dimethylformamide (100 ml) kept under an atmosphere of nitrogen, sodium hydride (1.0 g, 0.025 mol, 60% dispersion in oil) was carefully added. The reaction mixture was left stirring for 15 minutes. 1-Bromo-3-chloropropane (8.0 g, 0.05 mol) was added and the mixture was left stirring overnight. Ammonium chloride (2.0 g, 0.04 mol) was added, and after continued stirring for 30 minutes the solution was poured onto water (300 ml). The mixture was extracted with dichloromethane (2×200 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent evaporated. This afforded a residue which was purified by column chromatography on silica gel (250 g) using a mixture of n-heptane and ethyl acetate (9:1) as eluent. 4.4 g (80%) of 10-(3-chloropropyl)-10H-phenothiazine was obtained as an oil. Rf : 0.55 (SiO2 ; n-heptane/ethyl acetate=1:1).

Workup

  1. waitThe reaction mixture was left
  2. waitthe mixture was left
  3. stirringstirring overnight
  4. stirringafter continued stirring for 30 minutes the solution
  5. additionwas poured onto water (300 ml)
  6. extractionThe mixture was extracted with dichloromethane (2×200 ml)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customThis afforded a residue which
  11. customwas purified by column chromatography on silica gel (250 g)
  12. additiona mixture of n-heptane and ethyl acetate (9:1) as eluent

Sources & evidence

ORD record
ord-c2321218af394d718e8b6b92bb1f0326
Source dataset
uspto-grants-1997_09
Patent number
US05668129

Reaction notes

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