Dicyclohexylcarbodiimide → 4-Amidino-2-benzoylphenyl 4-dimethylaminobenzoate methanesulfonate

HRID 1981448Notes

Reaction equation

HRID 1981448 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:28][S:29]([O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39](=[NH:41])[NH2:40])=[CH:35][C:34]=1[C:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:31])=[O:30]>N1C=CC=CC=1>[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:33]2[CH:38]=[CH:37][C:36]([C:39](=[NH:40])[NH2:41])=[CH:35][C:34]=2[C:42](=[O:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 120924-(Dimethylamino)benzoic acidHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Product 1

HCID 202471194-Amidino-2-benzoylphenyl 4-dimethylaminobenzoate methanesulfonateYield 24.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 50 ml of dried pyridine, was dissolved 1.65 g of 4-dimethylaminobenzoic acid followed by the addition of 3.1 g of DCC. After 30 minutes of stirring, 3.36 g of 4-amidino-2-benzoylphenol methanesulfonate was added to the mixture and the mixture was further stirred overnight. The reaction mixture was removed of the insolubles by filtration and recrystallized from ethanol to yield 1.2 g of 4-amidino-2-benzoylphenyl 4-dimethylaminobenzoate methanesulfonate.

Workup

  1. waitthe mixture was further stirred overnight
  2. customThe reaction mixture was removed of the insolubles by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-864b6f87bc3443ed9e1e4346cdad333b
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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