Benzoic Acid → Benzamide

HRID 234656Notes

Reaction equation

HRID 234656 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC([N:16]=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH2:16])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To compound L (250 mg, 0.598 mmol) in CH2Cl2 (8 mL) was added benzoic acid (100 mg, 0.819 mmol), DCC (200 mg, 0.971 mmol), and DMAP (10 mg, 0.082 mmol) at room temperature. A heterogeneous mixture resulted after approximately 5 minutes and stirring was continued for an additional 3 hours. The contents were concentrated in vacuo and chromatographed on SiO2 (3% acetone-CH2Cl2) which afforded the benzamide contaminated with residual Ph3P. Repeated recrystallization of this material from Et2O afforded 198 mg (63%) of compound M as a pale off white solid.

Workup

  1. customA heterogeneous mixture resulted after approximately 5 minutes
  2. concentrationThe contents were concentrated in vacuo
  3. customchromatographed on SiO2 (3% acetone-CH2Cl2) which

Sources & evidence

ORD record
ord-c13cffdd588b49d681e86eff2af68727
Source dataset
uspto-grants-1997_01
Patent number
US05595998

Reaction notes

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