Water → HCID 18509279, compound

HRID 1356638Notes

Reaction equation

HRID 1356638 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:4]([C:20](=O)[NH2:21])[CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)(=[O:8])=[O:9])=[C:4]([C:20]#[N:21])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 18509237HCID 18509237, compound

Product 1

HCID 18509279HCID 18509279, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4′-chloro-2′-carbamoyl-N-methyl-p-toluenesulfonanilide (0.70 g (2.07 mmol)) in pyridine (3.0 ml), under cooling with ice and with stirring, trifluoroacetic anhydride (0.40 ml (2.83 mmol)) was added dropwise. The temperature of the reaction mixture was brought to room temperature and the mixture was stirred at the same temperature for 2 hours. Then, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid, water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Diisopropyl ether was added to the residue and crystals separated was filtered and washed to give 0.63 g (95%) of the title compound as white crystals.

Workup

  1. customwas brought to room temperature
  2. stirringthe mixture was stirred at the same temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with dilute hydrochloric acid, water and saturated sodium chloride solution
  5. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionDiisopropyl ether was added to the residue and crystals
  8. customseparated
  9. filtrationwas filtered
  10. washwashed

Sources & evidence

ORD record
ord-c94b7d49e8514ded80ee6e9136dc5a1d
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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