Nitrogen → HCID 67957872, compound

HRID 82811

Reaction equation

HRID 82811 reaction equation
N#N.Cl[CH2:4][C:5]1[N:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:8][CH:9]=1.[N+:15]([C:18]1[CH:22]=[N:21][NH:20][N:19]=1)([O-:17])=[O:16].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:15]([C:18]1[CH:22]=[N:21][N:20]([CH2:4][C:5]2[N:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:8][CH:9]=2)[N:19]=1)([O-:17])=[O:16]

Participants

8

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 10822129Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

Product 1

HCID 67957872HCID 67957872, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

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 ethyl 4-(chloromethyl)thiazole-2-carboxylate (WO 2009077990 A1) (2.16 g, 10.5 mmol) in DMF (15.0 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) (8.0 g of a 10% solution in DMF, 7.01 mmol) in DMF (15.0 mL) pre-treated for 30 min with DIPEA (1.82 mL, 2.33 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 washed with water (50 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA)) gave the title compound as a yellow oil. TLC: rf (7:3 hept-EA)=0.36. LC-MS-conditions 07: tR=0.76 min, [M+H]+=284.28.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. washthe aq. layer was washed with water (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (60:40 hept-EA))

Sources & evidence

ORD record
ord-98a13a8e4c63474f8817f5edd0f5d2f2
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Linked notes

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