Acetic Acid → HCID 20474269, compound

HRID 2295900Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8]([N:10]2[N:14]=[C:13]([CH3:15])[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N:22]1[N:23]=[CH:24][N:25]([CH2:27][C:28](OCC)=[O:29])[CH:26]=1.C(O)(=O)C.N1CCCCC1>C(O)C>[N:22]1[N:23]=[CH:24][N:25]([C:27]2[C:28](=[O:29])[O:1][C:2]3[C:3]([CH:4]=2)=[CH:6][CH:7]=[C:8]([N:10]2[N:14]=[C:13]([CH3:15])[C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:11]2)[CH:9]=3)[CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

15.0 g (50.0 mmols) of the Na salt of 2-hydroxy-4-(4-methyl-5-phenyl-2H-1,2,3-triazol-2-yl)-benzaldehyde, 7.75 g (50.0 mmols) of ethyl 1,2,4-triazol-4-yl-acetate, 1.50 g (25.0 mmols) of glacial acetic acid and 500 mg (6.00 mmols) of piperidine are refluxed in 70 ml of anhydrous ethanol for 8 hours under an N2 atmosphere. The mixture is rapidly filtered off under suction and the residue is washed with ethanol and water. Finally, the residue is again stirred with 100 ml of ethanol for 2 hours at 60° C., and the mixture is filtered off under suction and the residue is dried: 12.0 g (65%) of a pale yellow crystalline powder. Recrystallisation from dimethylformamide yields 9.64 g (52%) of 3-(1,2,4-triazol-4-yl)-7-(4-methyl-5-phenyl-2H-1,2,3-triazol-2-yl)-coumarin in the form of pale yellow microplatelets of melting point 324°-326° C. (decomposition).

Workup

filtrationThe mixture is rapidly filtered off under suction
washthe residue is washed with ethanol and water
filtrationthe mixture is filtered off under suction
customthe residue is dried
customRecrystallisation from dimethylformamide

Sources & evidence

ORD record: ord-bd728d40c1714dbfaf9076381fb8d3b4
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04426530

Reaction notes

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