Bromoacetyl bromide → HCID 21265963, compound

HRID 566306Notes

Reaction equation

HRID 566306 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].[Br:17][CH2:18][C:19](Br)=[O:20]>C1C=CC=CC=1>[Br:17][CH2:18][C:19]([NH:1][C:2]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5])=[O:20]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 10403952HCID 10403952, compound

Product 1

HCID 21265963HCID 21265963, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 18.7 g of 2-(2-amino-5-iodobenzoyl)pyridine (R. I. Fryer, P. Zhang & R. Rios, Synth.Commun. 1993, 23, 985-992) in 760 ml of benzene were added 10.2 ml of bromoacetyl bromide and the mixture was heated to reflux temperature for 20 h. After cooling the crystals are filtered off and these are then stirred for 30 min. in a mixture of 3 l of saturated aqueous sodium hydrogen (sic) carbonate solution and 1 l of dichloromethane. The aqueous phase was separated and extracted again with dichloromethane. The dichloromethane solutions were dried over sodium sulphate and evaporated. The dark brown crystalline residue (25 g) was chromatographed over 400 g of silica gel. With toluene/ethyl acetate 8:1 there were eluted 19.1 g of the desired product which was recrystallized from ethanol/diethyl ether. There were obtained 17.6 g of 2-[2-(bromoacetylamino)-5-iodobenzoyl]-pyridine, which was used without further purification for the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux temperature for 20 h
  3. temperatureAfter cooling the crystals
  4. filtrationare filtered off
  5. customThe aqueous phase was separated
  6. extractionextracted again with dichloromethane
  7. dry with materialThe dichloromethane solutions were dried over sodium sulphate
  8. customevaporated
  9. customThe dark brown crystalline residue (25 g) was chromatographed over 400 g of silica gel
  10. washWith toluene/ethyl acetate 8:1 there were eluted 19.1 g of the desired product which
  11. customwas recrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-77bf6f0ecf1d4d0482e0eeadf42b511a
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

Loading…