Bromoacetyl bromide → HCID 135604924, compound

HRID 11269Notes

Reaction equation

HRID 11269 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:15][C:14](=[O:16])[C:13]2=[C:17]([CH2:23][CH3:24])[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[N:12]2[N:11]=1)[CH3:2].[Br:25][CH2:26][C:27](Br)=[O:28].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:25][CH2:26][C:27]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:10]2[NH:15][C:14](=[O:16])[C:13]3=[C:17]([CH2:23][CH3:24])[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[N:12]3[N:11]=2)[CH:6]=1)=[O:28]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 1358567572-(2-Ethoxyphenyl)-5-ethyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one

Product 1

HCID 135604924HCID 135604924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution, cooled to 0° C., of 1 g (3.1 mmol) of the compound from example 17A in 80 ml of CH2Cl2 was admixed dropwise with 1.2 g (6.1 mmol) of bromoacetyl bromide and a little at a time with 1.2 g (9.1 mmol) of AlCl3. The reaction mixture was warmed to room temperature (30 min.) and then heated at reflux for 2 h and carefully poured into ice-water. Following extraction with CH2Cl2, drying over MgSO4 and concentration under reduced pressure, the residue was triturated with ether. This gave 1.33 g (33% pure according to LC-MS) of the desired product which was reacted further without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. extractionextraction with CH2Cl2
  4. dry with materialdrying over MgSO4 and concentration under reduced pressure
  5. customthe residue was triturated with ether
  6. customThis gave 1.33 g (33% pure according to LC-MS) of the desired product which was reacted further without further purification

Sources & evidence

ORD record
ord-1a9df976ff5240b3a21e1366d2833d10
Source dataset
uspto-grants-2006_08
Patent number
US07098207B2

Reaction notes

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