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

HRID 1154638Notes

Reaction equation

HRID 1154638 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

0.24 gm of a 55% sodium hydride dispersion in oil were added to a mixture of 1.35 gm (5 mol) of 7-bromo-8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one in 15 ml of dimethylsulfoxide at room temperature. After stirring the mixture at room temperature for 30 minutes and at a temperature between 35° and 40° C. for 10 minutes, the obtained solution was added to 0.79 gm (5.5 mol) of 1-bromo-3-chloro-propane in 5 ml of dimethylsulfoxide. After stirring the mixture at room temperature for 2 hours, it was poured into ice water, and the aqueous mixture was extracted four times with methylene chloride. The methylene chloride extracts were washed with water, dried and evaporated in vacuo. The residue was purified by chromatography on silica gel, using ethyl acetate as the eluant.

Workup

  1. waitat a temperature between 35° and 40° C. for 10 minutes
  2. stirringAfter stirring the mixture at room temperature for 2 hours
  3. extractionthe aqueous mixture was extracted four times with methylene chloride
  4. washThe methylene chloride extracts were washed with water
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f39b9450fba8415098c2eae71efcd8f3
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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