1-Bromo-3-chloropropane → HCID 13520688, compound

HRID 648965Notes

Reaction equation

HRID 648965 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:15]([O:16][CH3:17])=[CH:14][C:7]2[CH2:8][C:9](=[O:13])[NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22]>CS(C)=O>[Br:3][C:4]1[C:15]([O:16][CH3:17])=[CH:14][C:7]2[CH2:8][C:9](=[O:13])[N:10]([CH2:19][CH2:20][CH2:21][Cl:22])[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 13520687HCID 13520687, compound

Product 1

HCID 13520688HCID 13520688, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A 55% sodium hydride dispersion (0.24 g, 5.5 mmol) in oil is added to 7-bromo-8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one (1.35 g, 5 mmol) in dimethylsulfoxide (15 ml) and the mixture is stirred for half an hour at ambient temperature and for 10 minutes at 35°-40° C. The solution is added dropwise, with stirring, to 1-bromo-3-chloro-propane (0.79 g, 5.5 mmol) in dimethylsulfoxide (5 ml). Then the mixture is stirred for 2 hours at ambient temperature, poured into ice water and extracted (4 times) with methylene chloride. The methylene chloride extracts are washed several times with water, dried and evaporated in vacuo. The residue is purified over a silica gel column with ethyl acetate as eluant.

Workup

  1. additionThe solution is added dropwise
  2. stirringThen the mixture is stirred for 2 hours at ambient temperature
  3. extractionextracted (4 times) with methylene chloride
  4. washThe methylene chloride extracts are washed several times with water
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue is purified over a silica gel column with ethyl acetate as eluant

Sources & evidence

ORD record
ord-2544d9a7643f4f8b84edf0e3a5fe8cc9
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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