Water → Methyl 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylate

HRID 450507Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][N:16]=[N+:17]=[N-:18])[CH:11]=[CH:12][C:13]=1[Cl:14].[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.O>CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][N:16]2[C:21]([CH3:23])=[C:20]([C:19]([O:25][CH3:26])=[O:24])[N:18]=[N:17]2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of milled potassium carbonate (38.7 g, 0.28 mol) in DMSO (100 mL) was added (3,4-dichlorophenyl)methyl azide (Intermediate 3) (14 g, 0.07 mol) and methyl acetoacetate (12.1 g, 0.1 mol). The mixture was stirred at 40° C. for 48 hours. The mixture was poured into a mixture of ice and water (100 mL). The water was extracted with ethyl acetate (100 mL×2). The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by distillation to give the title compound as white solid crystals (14 g, 67%). LC/MS: m/z 301 (M+H)+, Rt: 1.97 min.

Workup

extractionThe water was extracted with ethyl acetate (100 mL×2)
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
distillationThe residue was purified by distillation

Sources & evidence

ORD record: ord-373e0a9c4cbb4ded808e5f9127086921
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486977B2

Reaction notes

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