Dicyclohexylcarbodiimide → HCID 59938236, compound

HRID 634846Notes

Reaction equation

HRID 634846 reaction equation
[C:1]1([CH2:10][C:11]([OH:13])=O)[O:2][CH:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[OH:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:18][C:17](=[O:25])[CH:16]=1.C1CCC(N=C=NC2CCCCC2)CC1.[Na].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C.C(O)C>[O:2]1[C:3]2[CH:4]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:1]1[CH2:10][C:11]([C:16]1[C:17](=[O:25])[O:18][C:19]2[C:24]([C:15]=1[OH:14])=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:13]

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 20325024HCID 20325024, compoundHCID 546829304-Hydroxycoumarin

Product 1

HCID 59938236HCID 59938236, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

1.76 g (10.0 mmol) of 2-benzofuranacetic acid, 1.62 g (10.0 mmol) of 4-hydroxy-coumarin and 2.27 g (11.1 mmol) of DCC were suspended in 50 ml of chloroform, then 130 mg (1.06 mmol) of DMAP added and stirring carried out overnight at 60° C. The reaction liquid was then cooled to room temperature and the insoluble material filtered off. The mother liquor was concentrated and the residue purified by column chromatography. The solid obtained was recrystallized from ethanol and Compound 16 (460 mg, 1.43 mmol, 14%) obtained. This was converted to the sodium salt with an equivalent quantity of sodium hydrogen carbonate.

Workup

  1. customThe reaction liquid
  2. filtrationthe insoluble material filtered off
  3. concentrationThe mother liquor was concentrated
  4. customthe residue purified by column chromatography
  5. customThe solid obtained
  6. customobtained

Sources & evidence

ORD record
ord-a07b7154d1874ec6ab34e217c0288449
Source dataset
uspto-grants-2001_02
Patent number
US06184245B2

Reaction notes

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