Bromoacetyl bromide → HCID 67443924, compound

HRID 1666700Notes

Reaction equation

HRID 1666700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:5][N:6]([CH3:11])[CH2:7][CH2:8][CH2:9][NH2:10].[Br:16][CH2:17][C:18](Br)=[O:19]>ClCCl>[BrH:16].[Br:16][CH2:17][C:18]([NH:10][CH2:9][CH2:8][CH2:7][N:6]([CH2:5][C:4]1[CH:12]=[CH:13][C:14]([Cl:15])=[C:2]([Cl:1])[CH:3]=1)[CH3:11])=[O:19]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 67443705HCID 67443705, compound

Product 1

HCID 67443924HCID 67443924, compoundYield 135.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

4.9 g (20 mmol) N-(3,4-Dichlorobenzyl)-N-(methyl)propan-1,3-diamine is dissolved in 50 ml dichloromethane. The solution is cooled to −10° C. and at that temperature 2 ml (23 mmol) bromoacetyl bromide in 12 ml dichloromethane is added to it dropwise. The reaction mixture is stirred at −10° C. for 10 minutes and at room temperature for 3 hours. Dichloromethane is poured off, the residue is stirred with 15 ml abs. ethanol, the precipitated crystals are filtered off, washed with ethanol and with ether to obtain 7 g title compound in the form of its hydrogen bromide salt. Mp.: 141° C.

Workup

  1. additionis added to it dropwise
  2. stirringthe residue is stirred with 15 ml abs
  3. filtrationethanol, the precipitated crystals are filtered off
  4. washwashed with ethanol and with ether

Sources & evidence

ORD record
ord-4b5a3b5468c04e46b9d7f8175d993d67
Source dataset
uspto-grants-2011_10
Patent number
US08044078B2

Reaction notes

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