Nitrogen → (4-((4-Nitro-2H-1,2,3-triazol-2-yl)methyl)thiazol-2-yl)methanol

HRID 82812Notes

Reaction equation

HRID 82812 reaction equation
N#N.[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[N:13]=[C:14]([C:17](OCC)=[O:18])[S:15][CH: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.C1(C)C=CC=CC=1>[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[N:13]=[C:14]([CH2:17][OH:18])[S:15][CH:16]=2)[N:7]=1)([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 947NitrogenHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 67957872Ethyl 4-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole-2-carboxylate

Product 1

HCID 67958245(4-((4-Nitro-2H-1,2,3-triazol-2-yl)methyl)thiazol-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of ethyl 4-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole-2-carboxylate (845 mg, 2.98 mmol) in THF (30 mL) was treated dropwise at 0° C. with DiBAL-H (11.3 mL of a 1.0 M solution in toluene, 11.3 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. Purification of the residue by FC (40:60 hept-EA)) gave the title compound as a yellow oil. TLC: rf (4:6 hept-EA)=0.25. LC-MS-conditions 07: tR=0.54 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
  6. customPurification of the residue by FC (40:60 hept-EA))

Sources & evidence

ORD record
ord-74a15ad6192c4b96b36b4e039f98d143
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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