Diisopropylcarbodiimide → N,N'-diisopropyl-O-(m-methoxycarbonylbenzyl)-isourea

HRID 980444Notes

Reaction equation

HRID 980444 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][OH:9])=[O:4].[CH:13]([N:16]=[C:17]=[N:18][CH:19]([CH3:21])[CH3:20])([CH3:15])[CH3:14]>CCCCCC>[CH:19]([NH:18][C:17](=[N:16][CH:13]([CH3:15])[CH3:14])[O:9][CH2:8][C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=1)([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 12734DiisopropylcarbodiimideHCID 155058Benzoic acid, 3-(hydroxymethyl)-, methyl ester

Product 1

HCID 14760215N,N'-diisopropyl-O-(m-methoxycarbonylbenzyl)-isoureaYield 96%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 4.75 g (28.6 mmols) of m-methoxycarbonylbenzyl alcohol and 3.6 g (28.6 mmols) of N,N'-diisopropylcarbodiimide was stirred with 50 mg (0.51 mmols) of cuprous chloride at room temperature for 24 hours. The reaction was then diluted with 10 ml of hexane and eluted through a short column of neutral alumina with 20% ethyl acetate-hexane to give 8.0 g (96%) of N,N'-diisopropyl-O-(m-methoxycarbonylbenzyl)-isourea as a colorless oil.

Workup

  1. washeluted through a short column of neutral alumina with 20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-0a4fd9bc53074be4b3f8a4084c95a706
Source dataset
uspto-grants-1987_01
Patent number
US04637999

Reaction notes

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