Hydrochloric Acid → 2-(2-Methoxyphenyl)-3-phenyl-2-[(1,2,4-triazol-1-yl)methyl]propanoic acid

HRID 1608771Notes

Reaction equation

[CH2:1]([C:8]1([CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:24].[K+].I[CH3:27].Cl>O.CO>[CH3:27][O:24][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:8]([CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([OH:10])=[O:17]

Participants

Conditions

Temperature: 25 °C

Procedure

To a clear solution of 3-benzyl-3-[(1,2,4-triazol-1-yl)methyl]-2(3H)-benzofuranone (11 g, 0.0360 mole) and methanol (100 mL), potassium hydroxide (45% solution) (0.5 g, 0.0750 mole) was added and the reaction mixture heated with stirring at reflux for 3 hours. The reaction mixture was then cooled to 25° C. and iodomethane (6.1 g, 0.0750 mole) added and the reaction mixture continued to stir at 50° C. for an additional 3 hours. The reaction solvent was then removed by distillation, and the residue stirred with hydrochloric acid (5 g, 0.37 mole) and 100 mL of water. The precipitated solid was filtered by suction and washed by 100 mL of hot ethyl acetate. The remaining solid was dried and gave 7.0 g, melting point 250°-252° C. (yield 57%), Example 95 of Table 1.

Workup

temperaturethe reaction mixture heated
temperatureat reflux for 3 hours
stirringto stir at 50° C. for an additional 3 hours
customThe reaction solvent was then removed by distillation
filtrationThe precipitated solid was filtered by suction
washwashed by 100 mL of hot ethyl acetate
customThe remaining solid was dried
customgave 7.0 g, melting point 250°-252° C. (yield 57%), Example 95 of Table 1

Sources & evidence

ORD record: ord-9c9e3fb6d4654080a0e970b1ac0b5d84
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05397768

Reaction notes

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