Hydrochloric Acid → HCID 18958063, compound

HRID 2379189Notes

Reaction equation

HRID 2379189 reaction equation
[H-].[Na+].[N+:3]([CH3:6])([O-:5])=[O:4].[F:7][C:8]1[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:9]=1[C:10](O)=[O:11].Cl>CN(C)C=O>[F:7][C:8]1[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:9]=1[C:10](=[O:11])[CH2:6][N+:3]([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 24758Sodium hydrideHCID 18958067HCID 18958067, compound

Product 1

HCID 18958063HCID 18958063, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% Sodium hydride (3.0 g) was suspended in 20 ml of N,N-dimethylformamide, then 8.4 g of nitro-methane was gradually dropped thereinto with ice-cooling and stirring and the mixture was stirred at room temperature for 30 minutes. 2-Fluoro-5-methanesulfonylaminobenzoic acid (8.0 g) and 6.7 g of N,N'-carbonyldiimidazole were dissolved in 30 ml of N,N-dimethylformamide and the solution was made to react at room temperature for 1 hour. The reaction mixture was added, with ice-cooling, to the solution obtained hereinbefore and the mixture was stirred at room temperature for 2 hours. Then, the mixture was poured into ice water, acidified with hydrochloric acid and the crystals separated out therefrom were filtered, washed with small amount of ethanol and dried to give 8.2 g of 4'-fluoro-3'-(2-nitroacetyl)-methanesulfonanilide, m.p. 174°-176 ° C.

Workup

  1. temperaturewith ice-cooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customto react at room temperature for 1 hour
  4. additionThe reaction mixture was added, with ice-
  5. temperaturecooling, to the solution
  6. customobtained hereinbefore
  7. stirringthe mixture was stirred at room temperature for 2 hours
  8. customthe crystals separated out
  9. filtrationtherefrom were filtered
  10. washwashed with small amount of ethanol
  11. customdried

Sources & evidence

ORD record
ord-4082896c27f640a8825d37041e607ef8
Source dataset
uspto-grants-1994_11
Patent number
US05360822

Reaction notes

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