Benzoic Acid → N-(2-aminophenyl)benzamide

HRID 430032Notes

Reaction equation

HRID 430032 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1([NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].FC(F)(F)C(O)=O>CS(C)=O>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:17][C:1](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 6422Trifluoroacetic acidHCID 7243O-Phenylenediamine

Product 1

HCID 759408N-(2-aminophenyl)benzamideYield 59.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.62 g (10 mmole) of N,N′-carbonyldiimidazole were added to a dimethyl sulfoxide (10 ml) solution including 1.12 g (10 mmole) of benzoic acid, followed by stirring at room temperature for 1 hour. After the addition of 2.16 g (20 mmole, 2 equivalents) of 1,2-phenylenediamine, 1.9 ml of trifluoroacetic acid were added dropwise at room temperature. After reaction had been further carried out at room temperature for 15 hours, a post-treatment was performed in the same manner as in Example 6 to obtain 1.27 g (yield: 59%) of N-(2-aminophenyl)benzamide.

Workup

  1. additionwere added dropwise at room temperature
  2. customAfter reaction
  3. waithad been further carried out at room temperature for 15 hours

Sources & evidence

ORD record
ord-18f931a5b2e64e3eba60a5611f30c625
Source dataset
uspto-grants-2001_11
Patent number
US06320078B1

Reaction notes

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