Triethylamine → HCID 54275004, compound

HRID 1607146Notes

Reaction equation

HRID 1607146 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C:4](Cl)=[O:5].[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][CH3:33])[C:12]=1[OH:34])(=[O:10])[CH3:9].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:7])[C:4]([NH:23][C:22]1[C:24]([CH3:28])=[CH:25][C:26]([Br:27])=[C:20]([O:19][CH2:18][CH2:17][CH2:16][O:15][C:14]2[CH:29]=[CH:30][C:11]([C:8](=[O:10])[CH3:9])=[C:12]([OH:34])[C:13]=2[CH2:31][CH2:32][CH3:33])[CH:21]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 19851999HCID 19851999, compound

Product 1

HCID 54275004HCID 54275004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In the course of approximately 5 minutes a solution of 3.2 ml of chloro-oxalic acid methyl ester in 10 ml of methylene chloride is added dropwise to a solution, cooled to 0°, of 14.0 g (32 mmol) of 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-bromo-6-methylaniline and 4.9 ml of triethylamine in 140 ml of methylene chloride and the whole 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 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 methyl ester having a melting point of 92°-93°.

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-0300ef41dff840039997b0bb097c4ceb
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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