Diisopropylethylamine → HCID 53859290, compound

HRID 1632515Notes

Reaction equation

HRID 1632515 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:6](=[CH:10][C:11]([CH3:19])=[C:12]([C:14](=[O:18])[CH2:15][CH2:16][CH3:17])[CH:13]=1)[NH:7][CH2:8][CH3:9])[CH3:2].C(N(C(C)C)C(C)C)C.[CH2:30]([O:32][C:33](=[O:38])[CH2:34][C:35](Cl)=[O:36])[CH3:31]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:6](=[CH:10][C:11]([CH3:19])=[C:12]([C:14](=[O:18])[CH2:15][CH2:16][CH3:17])[CH:13]=1)[N:7]([CH2:8][CH3:9])[C:35](=[O:36])[CH2:34][C:33]([O:32][CH2:30][CH3:31])=[O:38])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 118931Ethyl 3-chloro-3-oxopropionate2×HCID 54367973HCID 54367973, compound

Product 1

HCID 53859290HCID 53859290, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

13.86 g of the above anthranilic acid ethyl ester are dissolved in 140 ml of absolute toluene and 6.45 g of ethyl diisopropylamine are added. A solution of 7.6 g of chlorocarbonylacetic acid ethyl ester in 75 ml of absolute toluene is added dropwise at room temperature to this solution over a period of 30 minutes. After stirring for 10 hours at room temperature, a further 7.6 g of chlorocarbonylacetic acid ethyl ester in toluene are added dropwise in the course of 15 minutes and the mixture is stirred for a further 15 hours at room temperature. The reaction mixture is washed with water, sodium bicarbonate solution and water, dried over anhydrous sodium sulphate, filtered and concentrated to dryness by evaporation in vacuo. In this manner N-ethyl-5-butyryl-4-methyl-N-(1'-oxo-2'-ethoxycarbonylethyl)-anthranilic acid ethyl ester is obtained in the form of a pale yellow oil, which is further processed without further purification.

Workup

  1. stirringthe mixture is stirred for a further 15 hours at room temperature
  2. washThe reaction mixture is washed with water, sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness by evaporation in vacuo

Sources & evidence

ORD record
ord-474bf41aecc84830aefcc45e8559cd35
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

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