Triethylamine → HCID 54364491, compound

HRID 1607154Notes

Reaction equation

HRID 1607154 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]([Cl:28])=[CH:25][C:26]=2[CH3:27])[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]([Cl:28])=[CH:25][C:26]([CH3:27])=[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 19851936HCID 19851936, compound

Product 1

HCID 54364491HCID 54364491, 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 7.0 g (17.8 mmol) of 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-methyl-6-chloroaniline and 22.2 g (21.4 mmol) of triethylamine in 100 ml of methylene chloride. The reaction mixture is stirred for a further 90 minutes at room temperature, 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]-4-methyl-6-chlorophenyl}-oxamic acid methyl ester having a melting point of 101°-102°.

Workup

  1. additionpoured 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-fa8aa3ed05274775a3444f470dd86d17
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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