Pyridine → HCID 21701326, compound

HRID 1596350Notes

Reaction equation

HRID 1596350 reaction equation
[NH2:1][C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[O:5].N1C=CC=CC=1.[Br:24][CH2:25][C:26](Br)=[O:27]>C(Cl)Cl.C(OCC)(=O)C>[Br:24][CH2:25][C:26]([NH:1][C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[O:5])=[O:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 21701265HCID 21701265, compound

Product 1

HCID 21701326HCID 21701326, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-3-chloro-2′-fluorobenzophenone (4.80 g) and pyridine (3.04 g) in methylene chloride (100 ml) was added dropwise bromoacetyl bromide (3.42 ml) under stirring and cooling in an ice-bath. After the addition was completed, the mixture was stirred at ambient temperature for 0.5 hour and refluxed for 0.5 hour. The mixture was allowed to stand to cool to ambient temperature and evaporated in vacuo to give a residue, which was dissolved in ethyl acetate and washed with water three times and brine successively. After drying over magnesium sulfate and treating with active carbon, the solvent was removed in vacuo to give a crystalline mass. Pulverization in diisopropyl ether and collection by filtration afforded 2-(bromoacetylamino)-3-chloro-2′-fluorobenzophenone (5.86 g, 82.4% yield) as a white crystalline powder.

Workup

  1. temperaturecooling in an ice-bath
  2. additionAfter the addition
  3. stirringthe mixture was stirred at ambient temperature for 0.5 hour
  4. temperaturerefluxed for 0.5 hour
  5. customevaporated in vacuo
  6. customto give a residue, which
  7. washwashed with water three times and brine successively
  8. dry with materialAfter drying over magnesium sulfate
  9. additiontreating with active carbon
  10. customthe solvent was removed in vacuo
  11. customto give a crystalline mass
  12. customPulverization in diisopropyl ether and collection
  13. filtrationby filtration

Sources & evidence

ORD record
ord-fb8457cc496c497283e68bff57e043a5
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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