Dicyclohexylcarbodiimide → N-(3,3-dimethoxypropanoyl)-2-methoxy-5-acetoxy-aniline

HRID 1090702Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:13])[CH3:12])=[CH:6][C:4]=1[NH2:5].[CH3:14][O:15][CH:16]([O:21][CH3:22])[CH2:17][C:18](O)=[O:19].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH3:14][O:15][CH:16]([O:21][CH3:22])[CH2:17][C:18]([NH:5][C:4]1[CH:6]=[C:7]([O:10][C:11](=[O:13])[CH3:12])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:19]

Participants

Conditions

Temperature: 5 °C

Procedure

To a cooled solution (0° C.) of 2-methoxy-5-acetyloxy-aniline (5 g, 0.0276 mole), 3,3-dimethoxy-propanoic acid (5 g, 0.0373 mole) in 75 ml of methylene chloride was added DCC (5.7 g, 0.0276 mole) in 20 ml of methylene chloride. After completion of the addition, the solution was stirred for a further 4 hours. The reaction medium was concentrated to 25 ml, diluted with 200 ml of isopropyl ether, cooled to 5° C. and the resulting precipitate was isolated by filtration, giving N-(3,3-dimethoxypropanoyl)-2-methoxy-5-acetoxy-aniline 7.7 g (Yield=95%).

Workup

additionAfter completion of the addition
concentrationThe reaction medium was concentrated to 25 ml
additiondiluted with 200 ml of isopropyl ether
customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record: ord-a4ffffd22d0044a2b7baacaccbd1ace8
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05082847

Reaction notes

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