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

HRID 863558Notes

Reaction equation

HRID 863558 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-4baa9e1a61ed41fbabbafe5b2ffa25b2
Source dataset
uspto-grants-1998_02
Patent number
US05721254

Reaction notes

Loading…