Dicyclohexylcarbodiimide → HCID 178512545, compound

HRID 1589509Notes

Reaction equation

HRID 1589509 reaction equation
Cl.[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].C1CCC(N=C=NC2CCCCC2)CC1.CS([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41](=[NH:43])[NH2:42])=[CH:37][C:36]=1[C:44](=[O:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(=O)=[O:32]>N1C=CC=CC=1>[C:10](=[O:11])([OH:32])[OH:12].[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41](=[NH:43])[NH2:42])=[CH:37][C:36]=2[C:44](=[O:51])[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:11])=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 540991824-Amidino-2-benzoylphenol methanesulfonateHCID 178479383HCID 178479383, compound

Product 1

HCID 178512545HCID 178512545, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 11.6 g of 4-guanidinobenzoic acid hydrochloride in 180 ml of dried pyridine, while being cooled in ice, was added 13.2 g of DCC. After 30 minutes of stirring, 18.0 g of 4-amidino-2-benzoylphenol methanesulfonate was added, and the mixture was further stirred overnight at room temperature. A white solid substance precipitated from the reaction mixture was collected by filtration, washed with acetone, and dissolved in water. The aqueous solution was freed from the water-insoluble DCU by filtration and added to a saturated aqueous sodium bicarbonate solution, while being cooled in ice and stirred. The precipitated pale yellow crystals were collected by filtration, washed with water, then with acetone, and dried to yield 4-amidino-2-benzoylphenyl 4-guanidinobenzoate carbonate.

Workup

  1. waitthe mixture was further stirred overnight at room temperature
  2. customA white solid substance precipitated from the reaction mixture
  3. filtrationwas collected by filtration
  4. washwashed with acetone
  5. dissolutiondissolved in water
  6. filtrationThe aqueous solution was freed from the water-insoluble DCU by filtration
  7. additionadded to a saturated aqueous sodium bicarbonate solution
  8. temperaturewhile being cooled in ice
  9. stirringstirred
  10. filtrationThe precipitated pale yellow crystals were collected by filtration
  11. washwashed with water
  12. dry with materialwith acetone, and dried

Sources & evidence

ORD record
ord-8380dce1debb4f06a7b056075ad8cbd4
Source dataset
uspto-grants-1986_02
Patent number
US04570006

Reaction notes

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