Triethylamine → HCID 13799299, compound

HRID 652319Notes

Reaction equation

HRID 652319 reaction equation
[C:1](Cl)(=[O:6])[C:2]([O:4][CH3:5])=[O:3].[C:8]([C:11]1[CH:30]=[CH:29][C:14]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]([C:24]([CH3:28])=[CH:25][C:26]=2[Br:27])[NH2:23])=[C:13]([CH2:31][CH2:32][C:33]([F:36])([F:35])[F:34])[C:12]=1[OH:37])(=[O:10])[CH3:9].C(N(CC)CC)C>C(Cl)Cl>[C:8]([C:11]1[CH:30]=[CH:29][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])[C:24]([CH3:28])=[CH:25][C:26]=2[Br:27])=[C:13]([CH2:31][CH2:32][C:33]([F:34])([F:35])[F:36])[C:12]=1[OH:37])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 13799293HCID 13799293, compound

Product 1

HCID 13799299HCID 13799299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.36 ml (3.57 mmol) of methyl chlorooxalate in 5 ml of methylene chloride is added dropwise to a solution, cooled to 0°, of 1.75 g (3.57 mmol) of 3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-4-bromo-6-methyl-aniline (Example 1) and 0.55 ml (3.57 mmol) of triethylamine in 15 ml of methylene chloride in the course of 5 minutes. The reaction mixture is subsequently stirred at room temperature for 90 minutes and poured onto ice-water and the organic phase is separated off. The organic phase is washed with water, dried over sodium sulfate and concentrated under reduced pressure. Crystallisation of the residue from methylene chloride/ether gives methyl N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-4-bromo-6-methyl-phenyl}}-oxamate of melting point 139°-140°.

Workup

  1. additionpoured onto ice-water
  2. customthe organic phase is separated off
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customCrystallisation of the residue from methylene chloride/ether

Sources & evidence

ORD record
ord-8a91669e00384c75b468f88c54fd0923
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

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