Hydrochloric Acid → 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid

HRID 720634Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)=[O:4].[OH-].[Na+].O.Cl>CO>[C:10]([N:7]1[CH:8]=[N:9][C:5]([C:3]([OH:4])=[O:2])=[N:6]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester (500 mg, 1.35 mmol) in methanol at 25° C. was treated with a 1N aqueous sodium hydroxide solution (4.0 mL). The reaction was stirred at 25° C. for 24 h. At this time, the reaction mixture was poured into water (100 mL) and acidified with a 1N aqueous hydrochloric acid solution. This solution was extracted with ethyl acetate (2×150 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×150 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid (326 mg, 67%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ 8.37 (s, 1H), 7.39 (m, 9H), 7.05 (m, 6H), 3.82 (s, 3H).

Workup

extractionThis solution was extracted with ethyl acetate (2×150 mL)
washThe organics were washed with a saturated aqueous sodium chloride solution (1×150 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-820371716aa042b6827870bfb4f92b7d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135475B2

Reaction notes

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