1-Bromo-3-chloropropane → 10-(3-Chloropropyl)-10H-phenoxazine

HRID 1938196Notes

Reaction equation

HRID 1938196 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O: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[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67278Phenoxazine

Product 1

HCID 1008392610-(3-Chloropropyl)-10H-phenoxazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenoxazine (3.7 g, 0.02 mol) in dry dimethylformamide (100 ml) kept under an atmosphere of nitrogen, sodium hydride (1.2 g, 0.03 mol, 60% dispersion in oil) was carefully added. The reaction mixture was left stirring for 15 minutes. 1-Bromo-3-chloro-propane (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 in vacuo. 10-(3-Chloropropyl)-10H-phenoxazine was obtained in quantitative yield as an oil and used without further purification. Rf : 0.68 (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
  5. additionthe solution was 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 in vacuo

Sources & evidence

ORD record
ord-a8ed01c20dc44c659df327e7d931944b
Source dataset
uspto-grants-1997_12
Patent number
US05693649

Reaction notes

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