Nitrogen → HCID 67958309, compound

HRID 82808Notes

Reaction equation

HRID 82808 reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[S:13][CH:14]=[C:15]([C:17](OC)=[O:18])[N:16]=2)[N:7]=1)([O-:5])=[O:4].CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][OH:18])[N:16]=2)[N:7]=1)([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 947NitrogenHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 67958009Methyl 2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole-4-carboxylate

Product 1

HCID 67958309HCID 67958309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole-4-carboxylate (1.10 g, 4.08 mmol) in THF (30 mL) was treated dropwise at 0° C. with DiBAL-H (14.3 mL of a 1.0 M solution in THF, 14.3 mmol) and the resulting solution was stirred for 1 h at 0°. Rochelle's salt solution (100 mL) was added and the mixture was stirred for 1 h at rt. The aq. layer was extracted with EA (2×40 mL) and the combined org. layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.53 min; [M+H]+=241.95.

Workup

  1. stirringthe mixture was stirred for 1 h at rt
  2. extractionThe aq. layer was extracted with EA (2×40 mL)
  3. dry with materiallayers were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e5810005f7b64214a321cb81797c4865
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

Loading…