Water → HCID 18707160, compound

HRID 1489264Notes

Reaction equation

HRID 1489264 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([C:28]2[S:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][C:36](O)=[C:35]([C:40]([O:42][CH3:43])=[O:41])[CH:34]=3)[N:32]=2)[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH3:27])[CH3:17].C(N(CC)CC)C.O>ClCCl>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([C:28]2[S:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[C:35]([C:40]([O:42][CH3:43])=[O:41])[CH:34]=3)[N:32]=2)[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH3:27])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 18707277HCID 18707277, compound

Product 1

HCID 18707160HCID 18707160, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.5 g of trifluoromethanesulfonic acid anhydride was added to a solution of 10 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxyphenyl)thiazole dissolved in 100 ml of dichloromethane. Thereto was dropwise added 6 ml of triethylamine with stirring under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours. Thereto was added 40 ml of water for phase separation. The organic layer was dried and subjected to distillation to remove the solvent. The residue was recrystallized from ethanol to obtain 12.7 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-trifluoromethanesulfonyloxyphenyl)thiazole as a white powder.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours
  3. customfor phase separation
  4. customThe organic layer was dried
  5. distillationsubjected to distillation
  6. customto remove the solvent
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-4a038228f7504799a33499723a69fa67
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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