Dimethylformamide → 1-[4-[4-[2-(3,4-Dihydro-2-naphthyl)-4-oxazolylmethoxy]phenyl]butyl]-1,2,4-triazole

HRID 322369Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:4][CH:3]=1.Cl[CH2:18][C:19]1[N:20]=[C:21]([C:24]2[CH2:33][CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)[O:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:32][CH2:33][C:24]=1[C:21]1[O:22][CH:23]=[C:19]([CH2:18][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)=[CH:4][CH:3]=2)[N:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[4-(4-hydroxyphenyl)butyl]-1,2,4-triazole (450 mg), 4-chloromethyl-2-(3,4-dihydro-2-naphthyl) oxazole (565 mg), potassium carbonate (290 mg) and N,N-dimethylformamide (10 ml) was stirred for 6 hours at 80° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was subjected to a silica gel column chromatography. A crystalline product obtained from the fraction eluted with chloroform-methanol (50:1, v/v) was recrystallized from ethyl acetate-hexane to give 1-[4-[4-[2-(3,4-dihydro-2-naphthyl)-4-oxazolylmethoxy]phenyl]butyl]-1,2,4-triazole as colorless prisms, mp 96-97° C. The yield was 49%.

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried (MgSO4)
concentrationconcentrated
customA crystalline product obtained from the fraction
washeluted with chloroform-methanol (50:1
customv/v) was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-b28c9f916f5e43599bd2b154c6939c09
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211215B1

Reaction notes

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