Hydrochloric Acid → HCID 54325760, compound

HRID 2287370Notes

Reaction equation

HRID 2287370 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[C:7]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:6]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].Cl>CN(C)C=O>[CH3:1][O:2][C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[C:7]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:6]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 53746392HCID 53746392, compound

Product 1

HCID 54325760HCID 54325760, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (336 mg) was added to a solution of 320 mg of N-[6-chloro-5-(2-methoxyphenoxy)-2-trifluoromethyl-4-pyrimidinyl]-2-phenylethenesulfonamide in 10 ml of N,N-dimethylformamide followed by stirring overnight. The reaction mixture was poured into a mixture of ice and 1N hydrochloric acid and the solid separated out therefrom was collected by filtration. This solid was purified by a silica gel column chromatography (chloroform) and the resulting oil was crystallized from ether to give 210 mg of N-[6-methoxy-5-(2-methoxyphenoxy)-2-trifluoromethyl-4-pyrimidinyl]-2-phenylethenesulfonamide.

Workup

  1. customthe solid separated out
  2. filtrationtherefrom was collected by filtration
  3. customThis solid was purified by a silica gel column chromatography (chloroform)
  4. customthe resulting oil was crystallized from ether

Sources & evidence

ORD record
ord-d216cf2ffce14beba05510d80d2319a8
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

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