Potassium Carbonate → HCID 54298023, compound

HRID 2306483Notes

Reaction equation

HRID 2306483 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=[O:14])=[CH:9][CH:8]=1.[CH:22]1([NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH:4]=[CH:3][CH2:2][N:25]([CH:22]3[CH2:24][CH2:23]3)[C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])=[CH:8][CH:9]=2)=[O:14])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4298049HCID 4298049, compoundHCID 18434103HCID 18434103, compound

Product 1

HCID 54298023HCID 54298023, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 10 g of (E)-[4-(4-bromo-but-2-enyloxy)-phenyl]-(4-bromo-phenyl)-methanone, 7.47 g of N-cyclopropyl-2,2,2-trifluoro-acetamide, 6.7 g of potassium carbonate and 0.55 g of benzyltriethylammonium bromide in 200 ml of acetonitrile is heated to boiling while stirring for 7 h. After cooling to room temperature the suspension is filtered. The filtrate is concentrated and the residue is dissolved in a mixture of 500 ml of melthylene chloride and 50 ml of methanol and stirred with 50 g of a strongly acidic and strongly basic ion exchanger, subsequently filtered and washed with methylene chloride to give two phases. The organic phase is dried and concentrated. 11.5 g of N-[4-[4-(4-bromo-benzoyl)-phenoxy]-but-2-enyl]-N-cyclopropyl-2,2,2-trifluoroacetamide are obtained as a yellowish solid, MS: m/e 412 (M+-CF3, 1Br).

Workup

  1. temperatureis heated
  2. filtrationis filtered
  3. concentrationThe filtrate is concentrated
  4. dissolutionthe residue is dissolved in a mixture of 500 ml of melthylene chloride and 50 ml of methanol
  5. stirringstirred with 50 g of a strongly acidic and strongly basic ion exchanger
  6. filtrationsubsequently filtered
  7. washwashed with methylene chloride
  8. customto give two phases
  9. customThe organic phase is dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2a96cf361498440183d2ab0b04e7d192
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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