Triethylamine → HCID 53871632, compound

HRID 1607143Notes

Reaction equation

HRID 1607143 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C:4](Cl)=[O:5].[C:8]([C:11]1[CH:29]=[CH:28][C:14]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]([C:24]([CH3:27])=[CH:25][CH:26]=2)[NH2:23])=[C:13]([CH2:30][CH2:31][CH3:32])[C:12]=1[OH:33])(=[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]([CH3:27])=[CH:25][CH:26]=[C:20]([O:19][CH2:18][CH2:17][CH2:16][O:15][C:14]2[CH:28]=[CH:29][C:11]([C:8](=[O:10])[CH3:9])=[C:12]([OH:33])[C:13]=2[CH2:30][CH2:31][CH3:32])[CH:21]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 19852012HCID 19852012, compound

Product 1

HCID 53871632HCID 53871632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In the course of approximately 5 minutes a solution of 1.9 ml (21 mmol) of chloro-oxalic acid methyl ester in 8 ml of methylene chloride is added dropwise to a solution, cooled to 0°, of 7.5 g (21 mmol) of 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-6-methylaniline and 3.0 g (21 mmol) of triethylamine in 60 ml of methylene chloride. The reaction mixture is stirred for 90 minutes at room temperature, is poured onto ice-water and the organic phase is separated off. The methylene chloride phase is washed with water, dried over sodium sulphate and concentrated under reduced pressure. Crystallisation of the residue from methylene chloride/ether yields N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-6-methylphenyl}-oxamic acid methyl ester having a melting point of 125°-127°.

Workup

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

Sources & evidence

ORD record
ord-79bcceded424410baeccd6d0ba06672c
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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