Aniline → 2-{3-[3-(4-n-Butoxyphenyl)-3-oxopropanamido]-4-chlorophenylcarboxy}ethyl 3,5-di-t-butyl-4-hydroxybenzoate

HRID 845369Notes

Reaction equation

HRID 845369 reaction equation
NC1C=CC=CC=1.[C:8]([C:12]1[CH:13]=[C:14]([CH:31]=[C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:33]=1[OH:34])[C:15]([O:17][CH2:18][CH2:19][C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([NH2:30])[CH:24]=1)=[O:21])=[O:16])([CH3:11])([CH3:10])[CH3:9].[CH2:39]([O:43][C:44]1[CH:49]=[CH:48][C:47]([C:50](=[O:57])[CH2:51][C:52](OCC)=[O:53])=[CH:46][CH:45]=1)[CH2:40][CH2:41][CH3:42]>C1(C)C(C)=CC=CC=1>[C:35]([C:32]1[CH:31]=[C:14]([CH:13]=[C:12]([C:8]([CH3:10])([CH3:11])[CH3:9])[C:33]=1[OH:34])[C:15]([O:17][CH2:18][CH2:19][C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([NH:30][C:52](=[O:53])[CH2:51][C:50]([C:47]2[CH:48]=[CH:49][C:44]([O:43][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:45][CH:46]=2)=[O:57])[CH:24]=1)=[O:21])=[O:16])([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 6115AnilineHCID 201310072-(3-Amino-4-chlorophenylcarboxy)ethyl 3,5-di-t-butyl-4-hydroxybenzoateHCID 22153374HCID 22153374, compound

Product 1

HCID 867422642-{3-[3-(4-n-Butoxyphenyl)-3-oxopropanamido]-4-chlorophenylcarboxy}ethyl 3,5-di-t-butyl-4-hydroxybenzoateYield 82.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of the aniline from (c) (19.8 g, 44.2 mmole) and the β-ketoester from (e) (13.0 g, 44.2 mmole) in xylene (160 ml) were heated under reflux, using a Dean & Stark apparatus, for 5 hours. Over the final hour, the volume of the mixture was reduced to 75 ml by distillation. 60-80 petroleum ether (300 ml) was added with cooling and the solid collected by filtration. The product was isolated as a brown solid (24.2 g, 82%). m.p. 94-96%.

Workup

  1. temperatureunder reflux
  2. distillationOver the final hour, the volume of the mixture was reduced to 75 ml by distillation
  3. addition60-80 petroleum ether (300 ml) was added
  4. temperaturewith cooling
  5. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-900d318be2384966a6b04c0e4e67e827
Source dataset
uspto-grants-1988_07
Patent number
US04758501

Reaction notes

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