Sodium hydride → N,N-dimethyl-2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzenesulfonamide

HRID 375679

Reaction equation

HRID 375679 reaction equation
[H-].[Na+].[NH2:3][C:4]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:6]([O:8]CC)=O.[CH3:15][N:16]([CH3:30])[S:17]([C:20]1[CH:25]=[C:24]([N:26]=[C:27]=[O:28])[CH:23]=[CH:22][C:21]=1[Cl:29])(=[O:19])=[O:18]>O1CCCC1>[CH3:15][N:16]([CH3:30])[S:17]([C:20]1[CH:25]=[C:24]([N:26]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[NH:3][C:27]2=[O:28])[CH:23]=[CH:22][C:21]=1[Cl:29])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 136209Ethyl 3-amino-4,4,4-trifluoro-2-butenoateHCID 18993674N,N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide

Product 1

HCID 18993677N,N-dimethyl-2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

To 30 ml of dried tetrahydrofuran (THF) cooled to -5° C. was added, under nitrogen, 3.6 g of sodium hydride as a 60% dispersion mineral oil. To the stirred slurry was added a solution of 10 g of ethyl 3-amino-4,4,4-trifluoro-2-butenoate in 30 ml of THF over a period of 30 minutes. After stirring at -5° C. for 1 hour, the reaction mixture was cooled to -65° C. and a solution of N, N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide (Example A-4 above) in 30 ml of THF was added dropwise maintaining the temperature below -60° C. The mixture was stirred at -65° C. for 2 hours and allowed to warm to room temperature. After stirring for 17 hours, solvent was removed using a rotary evaporator. About 50 ml of water was added to the residue. The resulting mixture was filtered to remove a small amount of undissolved solid and the filtrate was acidified with hydrochloric acid. The resulting precipitate was filtered to give 13 g of the title compound as a beige solid, m.p. 281°-283° C.

Workup

  1. additionwas added, under nitrogen
  2. temperaturethe reaction mixture was cooled to -65° C.
  3. temperaturemaintaining the temperature below -60° C
  4. stirringThe mixture was stirred at -65° C. for 2 hours
  5. temperatureto warm to room temperature
  6. stirringAfter stirring for 17 hours
  7. customsolvent was removed
  8. customa rotary evaporator
  9. additionAbout 50 ml of water was added to the residue
  10. filtrationThe resulting mixture was filtered
  11. customto remove a small amount of undissolved solid
  12. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-cfa816a3e3654cc0a5c76a5f9d7681d5
Source dataset
uspto-grants-1996_01
Patent number
US05486610

Linked notes

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