Potassium Carbonate → HCID 54425757, compound

HRID 2057655Notes

Reaction equation

HRID 2057655 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 10442595Ethyl 3-(4-aminophenyl)propanoateHCID 53781721HCID 53781721, compound

Product 1

HCID 54425757HCID 54425757, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g. of ethyl 4-aminohydrocinnamate, 10.0 g. of 7-(3-bromophenyl)-1-methanesulfonyloxy-6-heptene (prepared by the method of Example 9), 4.2 g. of anhydrous powdered potassium carbonate and 40 ml. hexamethylphosphoramide is heated to 80° for 17 hours. The mixture is then cooled, diluted with water and extracted with ethyl ether. The ether extracts are washed with water, dried and evaporated. The residue is recrystallized from ethanol yielding the title compound as white crystals.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureThe mixture is then cooled
  3. extractionextracted with ethyl ether
  4. washThe ether extracts are washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from ethanol yielding the title compound as white crystals

Sources & evidence

ORD record
ord-bfdbba7516d8485e919616f652b40b63
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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