Dicyclohexylcarbodiimide → HCID 13176982, compound

HRID 371440Notes

Reaction equation

HRID 371440 reaction equation
[O:1]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:27][S:28]([O:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:42](=[NH:44])[NH2:43])[CH:38]=2)[CH:33]=1)(=[O:30])=[O:29]>N1C=CC=CC=1>[CH3:27][S:28]([OH:31])(=[O:30])=[O:29].[O:1]([CH2:8][C:9]([O:11][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:42](=[NH:43])[NH2:44])[CH:38]=2)[CH:33]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19188Phenoxyacetic AcidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13176982HCID 13176982, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.1 g of phenoxyacetic acid in 50 ml of pyridine, was added 2.2 g of DCC. The mixture was stirred at room temperature for 30 minutes, then admixed with 2.0 g of 6-amidino-2-naphthol methanesulfonate, and again stirred overnight at room temperature. The insolubles were removed by filtration, 500 ml of ethyl ether was added to the mother liquor and thoroughly stirred to precipitate a solid substance which was collected by filtration and recrystallized three times from methanol to obtain 0.3 g of 6-amidino-2-naphthyl phenoxyacetate methanesulfonate.

Workup

  1. customThe insolubles were removed by filtration, 500 ml of ethyl ether
  2. additionwas added to the mother liquor
  3. stirringthoroughly stirred
  4. customto precipitate a solid substance which
  5. filtrationwas collected by filtration
  6. customrecrystallized three times from methanol

Sources & evidence

ORD record
ord-b20184440c364b62b68abcf89c96e8ae
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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