Triethanolamine → HCID 54035976, compound

HRID 1607160Notes

Reaction equation

HRID 1607160 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[C:5](Cl)=[O:6])[CH3:2].[C:9]([C:12]1[CH:29]=[CH:28][C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=2)[NH2:24])=[C:14]([CH2:30][CH2:31][CH3:32])[C:13]=1[O:33][CH3:34])(=[O:11])[CH3:10].N(CCO)(CCO)CCO>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:8])[C:5]([NH:24][C:23]1[CH:25]=[CH:26][CH:27]=[C:21]([O:20][CH2:19][CH2:18][CH2:17][O:16][C:15]2[CH:28]=[CH:29][C:12]([C:9](=[O:11])[CH3:10])=[C:13]([O:33][CH3:34])[C:14]=2[CH2:30][CH2:31][CH3:32])[CH:22]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 7618TriethanolamineHCID 20884Ethoxalyl chlorideHCID 198519403-[3-(4-Acetyl-3-methoxy-2-n-propylphenoxy)-propoxy]-aniline

Product 1

HCID 54035976HCID 54035976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In the course of 10 minutes a solution of 3.45 ml of chloro-oxalic acid ethyl ester in 10 ml of methylene chloride is added dropwise to a solution of 9.2 g of 3-[3-(4-acetyl-3-methoxy-2-n-propylphenoxy)-propoxy]-aniline and 4.3 ml of triethanolamine in 90 ml of methylene chloride. After stirring for 5 hours at room temperature the mixture is poured onto water and extracted with methylene chloride. Concentration of the extracts by evaporation and recrystallisation of the residue from ether yields N-{3-[3-(4-acetyl-3-methoxy-2-n-propylphenoxy)-propoxy]-phenyl}-oxamic acid ethyl ester having a melting point of 91°-92°.

Workup

  1. additionis poured onto water
  2. extractionextracted with methylene chloride
  3. customConcentration of the extracts by evaporation and recrystallisation of the residue from ether

Sources & evidence

ORD record
ord-1c588282eaea4b6c95e7e19396044f0a
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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