Benzoyl chloride → HCID 23092005, compound

HRID 1393676Notes

Reaction equation

HRID 1393676 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O.ClCCl>[C:22]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 10264164Benzyl 1H-indole-5-carboxylate

Product 1

HCID 23092005HCID 23092005, compoundYield 117.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium hydride (58 mg) was added to a solution of benzyl 1H-indole-5-carboxylate (300 mg) in N,N-dimethylformamide (2 ml) with ice cooling, and then stirred for 30 minutes. Benzoyl chloride (202 mg) was added thereto, and the mixture was stirred for 2 hours. The reaction mixture was diluted with dichloromethane, and the organic phase was washed with 2 N hydrochloric acid, a saturated sodium bicarbonate solution and a saturated saline solution. The organic phase was dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give benzyl 1-benzoyl-1H-indole-5-carboxylate (500 mg, Y.:quant.) as pale orange crystals.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. washthe organic phase was washed with 2 N hydrochloric acid
  3. dry with materialThe organic phase was dried over sodium sulfate anhydrous
  4. concentrationThe product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a7a21af5cf84bcaaae5b556f66acca7
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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