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

HRID 1090702
Notes
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Reaction equation

HRID 1090702 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 103745043,3-dimethoxypropanoic AcidHCID 156769772-Methoxy-5-acetyloxy-aniline

Product 1

HCID 10424696N-(3,3-dimethoxypropanoyl)-2-methoxy-5-acetoxy-anilineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. additionAfter completion of the addition
  2. concentrationThe reaction medium was concentrated to 25 ml
  3. additiondiluted with 200 ml of isopropyl ether
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes