1H-1,2,4-Triazole → 4-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamide

HRID 1356460

Reaction equation

[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](OC)=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH2:30].N1C=NC=N1>CO>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:30][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of methyl 4-(4-biphenylylmethoxy)phenylacetate (1000 g), N,N-dimethylethylenediamine (795 g), and 1H-1,2,4-triazole (207 g) in methanol (2.0 l) was heated under reflux under nitrogen for 10 hr and was left to stand at room temperature over night. The reaction mixture was warmed to 60±2° C. and methanol (4.0 l) was added for 35 min. After stirring under reflux for additional one hr the reaction mixture was cooled to room temperature. The precipitate was collected by filtration and washed with methanol (2.0 l) to obtain the titled compound (1109 g).

Workup

temperaturewas heated
temperatureunder reflux under nitrogen for 10 hr
waitwas left
waitto stand at room temperature over night
temperatureunder reflux for additional one hr the reaction mixture
temperaturewas cooled to room temperature
filtrationThe precipitate was collected by filtration
washwashed with methanol (2.0 l)

Sources & evidence

ORD record: ord-dca06a8293254f2abe4d91e1757cb4bb
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586475B1

Linked notes

Loading…