Hydrochloric Acid → 4-[4-[8-(1,2,4-Triazol-1-yl)octyloxy]phenyl]benzoic acid

HRID 1386590Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Br[CH:9]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.Cl>CN(C)C=O.C(OCC)(=O)C.O>[N:3]1([CH2:32][CH2:31][CH2:30][CH2:29][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=3)=[CH:16][CH:15]=2)[CH:7]=[N:6][CH:5]=[N:4]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of sodium hydride (60% suspension in mineral oil) (0.296 g) in N,N-dimethylformamide (14 ml) was added 1,2,4-triazole (0.511 g) and 4-[4-(4-bromooctyloxy)phenyl]benzoic acid (1 g), and was stirred for 5 hours at 120° C. The reaction mixture was added to a mixture of water and ethyl acetate, and adjusted to pH 2.5 with conc. hydrochloric acid. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 4-[4-[8-(1,2,4-Triazol-1-yl)octyloxy]phenyl]benzoic acid (0.81 g).

Workup

dry with materialdried over magnesium sulfate
filtrationThe magnesium sulfate was filtered off
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-daf18af69aad49f1884ec75fab0cf3da
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265536B1

Reaction notes

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