Methyl chloroglyoxylate → methyl N-{{3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate

HRID 1086928Notes

Reaction equation

HRID 1086928 reaction equation
[C:1](Cl)(=[O:6])[C:2]([O:4][CH3:5])=[O:3].[C:8]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=2)[NH2:23])=[C:13]([CH2:29][CH2:30][C:31]([F:34])([F:33])[F:32])[C:12]=1[O:35][CH3:36])(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]([NH:23][C:1](=[O:6])[C:2]([O:4][CH3:5])=[O:3])[CH:24]=[CH:25][CH:26]=2)=[C:13]([CH2:29][CH2:30][C:31]([F:33])([F:32])[F:34])[C:12]=1[O:35][CH3:36])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 79846Methyl chloroglyoxylateHCID 198185853-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-aniline

Product 1

HCID 19818626methyl N-{{3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.45 ml of methyl chlorooxalate in 10 ml of methylene chloride is added dropwise to a solution of 9.2 g of 3-{3[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-aniline and 4.3 ml of triethanolpropy amine in 90 ml of methylene chloride in the course of 10 minutes. After stirring at room temperature for 5 hours, the mixture is poured onto water and extracted with methylene chloride. Evaporation of the extracts and recrystallisation of the residue from ether gives methyl N-{{3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate.

Workup

  1. additionthe mixture is poured onto water
  2. extractionextracted with methylene chloride
  3. customEvaporation of the extracts and recrystallisation of the residue from ether

Sources & evidence

ORD record
ord-72b26cf9de0c47359c2802b8edcf57f2
Source dataset
uspto-grants-1991_07
Patent number
US05032606

Reaction notes

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