2-Butene, 1,4-dibromo- → HCID 70663136, compound

HRID 2272942Notes

Reaction equation

HRID 2272942 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19][CH2:20][CH:21]=[CH:22][CH2:23]Br.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:23][CH:22]=[CH:21][CH2:20][Br:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 131802-Butene, 1,4-dibromo-HCID 24758Sodium hydrideHCID 4935691benzyl benzylcarbamate

Product 1

HCID 70663136HCID 70663136, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-benzyloxycarbonylbenzylamine (50 g), 1,4-dibromo-2-butene (44 g) and NaH (10.7 g, 60% in oil) in 350 ml of DMF is stirred at 0° C. for 1 h and then at 25° C. for 3 h. The reaction mixture is subjected to aqueous workup and the residue obtained is purified by chromatography over SiO2. The title compound is obtained as an oil having characterization data as indicated below.

Workup

  1. waitat 25° C. for 3 h
  2. customthe residue obtained
  3. customis purified by chromatography over SiO2

Sources & evidence

ORD record
ord-938e8a485779461b8d90f28e26b693fb
Source dataset
uspto-grants-2015_09
Patent number
US09120808B2

Reaction notes

Loading…