Acetyl chloride → HCID 14229722, compound

HRID 1761921Notes

Reaction equation

HRID 1761921 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:22])[C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][C:10]=2[CH:20]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[O:22])[C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:11][C:10]=2[CH:20]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 14229801HCID 14229801, compound

Product 1

HCID 14229722HCID 14229722, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 147 mg of acetyl chloride in 2 ml of toluene is added dropwise to a mixture of 522 mg of 2-piperidinoethyl 5-amino-2-phenylbenzofuran-7-carboxylate, 210 mg of sodium bicarbonate and 10 ml of ethyl acetate under ice-cooling. The mixture is stirred at the same temperature for 30 minutes and the reaction mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is recrystallized from ethyl acetate to give 467 mg of 2-piperidinoethyl 5-acetamido-2-phenylbenzofuran-7-carboxylate as pale yellow needles.

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c7817daa67ee475599f5dd71b9f538a1
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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