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

HRID 620307Notes

Reaction equation

HRID 620307 reaction equation
[C:1](Cl)(=[O:5])[C:2]([O-:4])=[O:3].[C:7]([C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=2)[NH2:22])=[C:12]([CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31])[C:11]=1[O:34][CH3:35])(=[O:9])[CH3:8].N(CCO)(CCO)[CH2:37]CO>C(Cl)Cl>[C:7]([C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]([NH:22][C:1](=[O:5])[C:2]([O:4][CH3:37])=[O:3])[CH:23]=[CH:24][CH:25]=2)=[C:12]([CH2:28][CH2:29][C:30]([F:31])([F:33])[F:32])[C:11]=1[O:34][CH3:35])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 7618TriethanolamineHCID 198185853-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-anilineHCID 21988599Chlorooxoacetate

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 metjhyl 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 triethanolamine 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-b0e1ea602bb34fc98935f101d7097dfa
Source dataset
uspto-grants-1989_04
Patent number
US04820726

Reaction notes

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