Triethylamine → HCID 53734811, compound

HRID 1607151Notes

Reaction equation

HRID 1607151 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[C:5](Cl)=[O:6])[CH3:2].[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][CH3:34])[C:13]=1[OH:35])(=[O:11])[CH3:10].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:8])[C:5]([NH:24][C:23]1[C:25]([CH3:29])=[CH:26][C:27]([Br:28])=[C:21]([O:20][CH2:19][CH2:18][CH2:17][O:16][C:15]2[CH:30]=[CH:31][C:12]([C:9](=[O:11])[CH3:10])=[C:13]([OH:35])[C:14]=2[CH2:32][CH2:33][CH3:34])[CH:22]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 19851999HCID 19851999, compound

Product 1

HCID 53734811HCID 53734811, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In the course of approximately 5 minutes a solution of 12.3 ml of chloro-oxalic acid ethyl ester in 30 ml of methylene chloride is added dropwise to a solution, cooled to 0° C., of 43.6 g (100 mmol) of 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-bromo-6-methylaniline and 15.3 ml of triethylamine in 400 ml of methylene chloride and the whole is then stirred for a further 90 minutes at room temperature. The reaction mixture is poured onto ice-water and the organic phase is separated off, washed with water, dried over sodium sulphate and concentrated under reduced pressure. Crystallisation from ethyl acetate/ether/petroleum ether yields N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-bromo-6-methylphenyl}-oxamic acid ethyl ester having a melting point of 100°-102°.

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 sulphate
  5. concentrationconcentrated under reduced pressure
  6. customCrystallisation from ethyl acetate/ether/petroleum ether

Sources & evidence

ORD record
ord-22135aa31d8f4b9b8abed9bddf577e4d
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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