Triethylamine → HCID 19818588, compound

HRID 652323Notes

Reaction equation

HRID 652323 reaction equation
[C:1](Cl)(=[O:7])[C:2]([O:4][CH2:5][CH3:6])=[O:3].[C:9]([C:12]1[CH:31]=[CH:30][C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]([C:25]([CH3:29])=[CH:26][C:27]=2[Br:28])[NH2:24])=[C:14]([CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:13]=1[OH:38])(=[O:11])[CH3:10].C(N(CC)CC)C>C(Cl)Cl>[C:9]([C:12]1[CH:31]=[CH:30][C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]([NH:24][C:1](=[O:7])[C:2]([O:4][CH2:5][CH3:6])=[O:3])[C:25]([CH3:29])=[CH:26][C:27]=2[Br:28])=[C:14]([CH2:32][CH2:33][C:34]([F:35])([F:36])[F:37])[C:13]=1[OH:38])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 13799293HCID 13799293, compound

Product 1

HCID 19818588HCID 19818588, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 12.3 ml of ethyl chlorooxalate in 30 ml of methylene chloride is added dropwise to a solution, cooled to 0° C., of 43.6 g of 3-{3-[4-acetyl-3-hydroxy-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-4-bromo-6-methylaniline and 15.3 ml of triethylamine in 400 ml of methylene chloride in the course of about 5 minutes and the mixture is then stirred at room temperature for a further 90 minutes. The reaction mixture is poured onto ice-water and the organic phase is separated off, washed with water, dried over sodium sulfate and concentrated under reduced pressure. Crystallisation from ethyl acetate/ether/petroleum ether gives ethyl N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-4-bromo-6-methyl-phenyl}}-oxamate.

Workup

  1. additionThe reaction mixture is poured onto ice-water
  2. customthe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customCrystallisation from ethyl acetate/ether/petroleum ether

Sources & evidence

ORD record
ord-15fb54c99961491cbe8884caf1f1eaef
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

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