2,4-Difluorobenzoyl chloride → HCID 10451647, compound

HRID 1087221Notes

Reaction equation

HRID 1087221 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([NH2:15])[CH:5]=1)(=[O:3])[CH3:2].[F:16][C:17]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>N1C=CC=CC=1>[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([NH:15][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:17]=2[F:16])[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5880812,4-Difluorobenzoyl chlorideHCID 10263173HCID 10263173, compound

Product 1

HCID 10451647HCID 10451647, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4'-acetyl-2'-aminomethanesulfonanilide (1.6 g) and 2,4-difluorobenzoyl chloride (1.5 g) in pyridine (15 ml) was stirred at 0° C. for 3 hours. The mixture was evaporated and the residue was stirred with 5% sodium hydroxide (40 ml) for 1 hour at room temperature. The mixture was washed with toluene, and the aqueous layer was acidified with hydrochloric acid. The precipitates obtained were recrystallized from a mixture of acetone and ethyl acetate (1:1) to give pale brown needles of N-(5-acetyl-2-methanesulfonamidophenyl)-2,4-difluorobenzamide (1.3 g).

Workup

  1. customThe mixture was evaporated
  2. stirringthe residue was stirred with 5% sodium hydroxide (40 ml) for 1 hour at room temperature
  3. washThe mixture was washed with toluene
  4. customThe precipitates obtained
  5. customwere recrystallized from a mixture of acetone and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-f376cbfafc864185a99c3b205ae215b9
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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