3-Nitrobenzaldehyde → N-{2-[2-(3-nitrobenzyliden)acetoacetoxy]ethyl}-N-cyclohexyl-4-(6-carbostyriloxy)butyramide

HRID 1284915Notes

Reaction equation

HRID 1284915 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][N:21]([CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[C:22](=[O:38])[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[CH:31]=[CH:30]2)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][N:21]([CH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1)[C:22](=[O:38])[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[CH:31]=[CH:30]2)=[O:17])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 20250808N-(2-acetoacetoxyethyl)N-cyclohexyl-4-(6-carbostyriloxy)butyramide

Product 1

HCID 54415444N-{2-[2-(3-nitrobenzyliden)acetoacetoxy]ethyl}-N-cyclohexyl-4-(6-carbostyriloxy)butyramideYield 5.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 10 ml of pyridine were added 0.9 g of 3-nitrobenzaldehyde and 2.7 g of N-(2-acetoacetoxyethyl)-N-cyclohexyl-4-(6-carbostyriloxy)butyramide, and the mixture was heated at 90°-100° C. for 20 hours. After cooling the reaction mixture was extracted with chloroform, and the chloroform layer was washed with a saturated aqueous solution of potassium hydrogensulfate and with a saturated aqueous solution of sodium chloride, then was dried with anhydrous magnesium sulfate. After being concentrated, the residue was purified by a silica gen column chromatography (eluant: chloroform/methanol=100/1), then the eluate was dried under vacuum condition to yield 0.2 g of N-{2-[2-(3-nitrobenzyliden)acetoacetoxy]ethyl}-N-cyclohexyl-4-(6-carbostyriloxy)butyramide in the form a brown oily substance.

Workup

  1. temperaturethe mixture was heated at 90°-100° C. for 20 hours
  2. temperatureAfter cooling the reaction mixture
  3. extractionwas extracted with chloroform
  4. washthe chloroform layer was washed with a saturated aqueous solution of potassium hydrogensulfate and with a saturated aqueous solution of sodium chloride
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. concentrationAfter being concentrated
  7. customthe residue was purified by a silica gen column chromatography (eluant: chloroform/methanol=100/1)
  8. customthe eluate was dried under vacuum condition

Sources & evidence

ORD record
ord-e62b79550337421bb95d3f44fa9ef0ff
Source dataset
uspto-grants-1986_01
Patent number
US04564619

Reaction notes

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