Dicyclohexylcarbodiimide → HCID 15052024, compound

HRID 329568Notes

Reaction equation

HRID 329568 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[CH2:23][O:22]2)=[CH:16][CH:15]=1)=O)([OH:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[C:1]1(=[O:3])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH:10]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25](=[O:26])[C:24]([CH3:27])([CH3:28])[CH2:23][O:22]3)=[CH:16][CH:15]=2)[O:2]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 15052016HCID 15052016, compound

Product 1

HCID 15052024HCID 15052024, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.57 gram (0.0015 mole) of 2-[[4-[(2-carboxyphenylmethyl)carbonylamino]phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone in 100 mL of toluene was cooled in an ice bath, and, with stirring, 0.33 gram (0.0016 mole) of dicyclohexylcarbodiimide was added in one portion. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it was stirred for 16 hours. The resultant solid was collected by filtration to yield 0.60 gram of 2-[[4-[(1H-2-benzopyran-1-one-3-yl)amino]phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 175°-177° C.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. stirringwas stirred for 16 hours
  3. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-ec648fc7aae44292a197c6bb9386d8b1
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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