Triethylamine → O-(3,5-Di-tert-butyl-4-hydroxyhydrocinnamoyl)-N,N-dibenzylhydroxylamine

HRID 477607

Reaction equation

C(Cl)(=O)C(Cl)=O.[C:7]([C:11]1[CH:12]=[C:13]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])([CH3:10])([CH3:9])[CH3:8].[CH2:27]([N:34]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>>[C:7]([C:11]1[CH:12]=[C:13]([CH:14]=[C:15]([C:18]([CH3:19])([CH3:20])[CH3:21])[C:16]=1[OH:17])[CH2:22][CH2:23][C:24]([O:26][N:34]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:25])([CH3:10])([CH3:8])[CH3:9]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 65578Oxalyl chloride

HCID 69297Dibenzylhydroxylamine

HCID 883893-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acid

Product 1

HCID 14875968O-(3,5-Di-tert-butyl-4-hydroxyhydrocinnamoyl)-N,N-dibenzylhydroxylamineYield 77%

Procedure

The procedure of Example II is followed using 3.17 g (25 mmol) of oxalyl chloride, 6.96 g (25 mmol) of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoic acid, 5.33 g (25 mmol) of N,N-dibenzylhydroxylamine, and 2.53 g (25 mmol) of triethylamine. The residue is recrystallized from petroleum ether to give 9.06 g (77%) of a white solid: mp 93°-95.5° C.

Workup

customThe residue is recrystallized from petroleum ether

Sources & evidence

ORD record: ord-0801c561e03d4a38bf7a910bfb4bb893
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04888444

Linked notes

Loading…