Trityl chloride → Ethyl (1-triphenylmethyl-1H-1,2,4-triazol-3-yl)acetate

HRID 566244Notes

Reaction equation

[NH:1]1[CH:5]=[N:4][C:3]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:2]1.[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>CN(C=O)C>[C:12]1([C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:1]2[CH:5]=[N:4][C:3]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:2]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Ethyl (1H-1,2,4-triazol-3-yl)acetate (2.83 g) was dissolved in DMF (40 ml). To the solution were added triphenyl methyl chloride (5.08 g) and triethylamine (2.55 ml). The mixture was stirred for 3 hours at 25° C. The reaction mixture was added to ice-water (150 ml), which was subjected to extraction with ethyl ether (100 ml). The organic layer was washed twice with water (150 ml), which was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The concentrate was purified by means of a column chromatography (carrier: silica gel, 150 g, developing solvent: ethyl acetate-hexane, 1:1) to afford the title compound (2.56 g) as a crystalline product, m.p.117-119° C.

Workup

extractionwas subjected to extraction with ethyl ether (100 ml)
washThe organic layer was washed twice with water (150 ml), which
dry with materialwas dried over anhydrous magnesium sulfate
concentrationfollowed by concentration under reduced pressure
customThe concentrate was purified by means of a column chromatography (carrier: silica gel, 150 g, developing solvent: ethyl acetate-hexane, 1:1)

Sources & evidence

ORD record: ord-79bcede3c9ec4d8babb3b4ba8296cbe6
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174877B1

Reaction notes

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