Dicyclohexylcarbodiimide → 4-Amidino-2-benzoylphenyl 4-acetylaminobenzoate

HRID 1981445Notes

Reaction equation

HRID 1981445 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:34]1[CH:39]=[CH:38][C:37]([C:40](=[NH:42])[NH2:41])=[CH:36][C:35]=1[C:43](=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=O)=O>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][C:34]2[CH:39]=[CH:38][C:37]([C:40](=[NH:41])[NH2:42])=[CH:36][C:35]=2[C:43](=[O:50])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19266p-Acetamidobenzoic acidHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Product 1

HCID 131784794-Amidino-2-benzoylphenyl 4-acetylaminobenzoateYield 22.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.79 g of 4-acetylaminobenzoic acid in 50 ml of dried pyridine, was added 3.1 g of DCC. The mixture was stirred for 30 minutes while being cooled in ice. After addition of 3.36 g of 4-amidino-2-benzoylphenol methanesulfonate, the mixture was further stirred overnight. The reaction mixture was removed of the insolubles and mixed with ethyl ether to obtain a colorless solid substance which on recrystallization from methanol yielded 0.9 g of colorless crystals of 4-amidino-2-benzoylphenyl 4-acetylaminobenzoate methanesulfonate.

Workup

  1. temperaturewhile being cooled in ice
  2. waitthe mixture was further stirred overnight
  3. customThe reaction mixture was removed of the insolubles
  4. additionmixed with ethyl ether
  5. customto obtain a colorless solid substance which
  6. customon recrystallization from methanol

Sources & evidence

ORD record
ord-a609303b90d3444fa307d5cdc41092bc
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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