Water → HCID 86703319, compound

HRID 2410003Notes

Reaction equation

HRID 2410003 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH3:14])=[O:4].S(Cl)([Cl:20])(=O)=O.O>C(Cl)(Cl)Cl>[Cl:20][C:9]1[C:10]([O:12][CH3:13])=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])=[C:7]([CH3:14])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 86703318HCID 86703318, compound

Product 1

HCID 86703319HCID 86703319, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2,2,2-Trifluoro-N-(5-methoxy-2-methylphenyl)acetamide (8.16 g) in chloroform (35 mL) was added sulfuryl chloride (3.12 mL) under ice-cooling, and the mixture was stirred overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the residue was added hexane, and the mixture was stirred at room temperature for 1 hour. The precipitate was collected by filtration, washed with hexane, and then dried under reduced pressure to obtain the title compound (7.02 g). 1H-NMR (CDCl3) δ ppm: 2.23 (3H, s), 3.90 (3H, s), 7.24 (1H, s), 7.59 (1H, s), 7.60-7.82 (1H, br).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added hexane
  7. stirringthe mixture was stirred at room temperature for 1 hour
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with hexane
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-af259ed0c7c2404c9f393d4b8d9e2cdc
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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