Nitrogen → Methyl 2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole-4-carboxylate

HRID 82807Notes

Reaction equation

N#N.Cl[CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1.[N+:14]([C:17]1[CH:21]=[N:20][NH:19][N:18]=1)([O-:16])=[O:15].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:14]([C:17]1[CH:21]=[N:20][N:19]([CH2:4][C:5]2[S:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=2)[N:18]=1)([O-:16])=[O:15]

Participants

Conditions

Temperature: 50 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(chloromethyl)thiazole-4-carboxylate (S. A. Hermitage et al. Organic Process Research & Development, 5, 37-44, 2001) (2.05 g, 10.7 mmol) in DMF (20.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (T. E. Eagles et al. Organic preparations and procedures 2 (2), 117-119, 1970; P. N. Neuman J. Heterocycl. Chem. 8, 51-56, 1971) (11.53 g of a 8% solution in DMF, 9.70 mmol) in DMF (20.0 mL) pre-treated for 30 min with DIPEA (3.21 mL, 19.4 mmol) and the reaction mixture was stirred overnight at 50° C. Water (50 mL), followed by EA (50 mL) was added. The layers were separated and the aq. layer was extracted with EA (2×50 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (gradient from 60:40 hept-EA to 50:50 hept-EA)) gave the title compound as a yellow solid. TLC: rf (6:4 hept-EA)=0.31. LC-MS-conditions 07: tR=0.67 min, [M+H]+=270.21.

Workup

additionwas added
customThe layers were separated
extractionthe aq. layer was extracted with EA (2×50 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (gradient from 60:40 hept-EA to 50:50 hept-EA))

Sources & evidence

ORD record: ord-4bcd5efe13d84d77a5045b79702d87f3
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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