Water → HCID 178490919, compound

HRID 2046995Notes

Reaction equation

HRID 2046995 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17].[C:19](=O)(OCC)[O:20]CC.CC(C)([O-])C.[K+].O>C1COCC1>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][N:6]2[C:2]3[N:1]=[C:19]([OH:20])[N:18]=[C:16]([OH:17])[C:3]=3[N:4]=[N:5]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7766Diethyl CarbonateHCID 339321HCID 339321, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 178490919HCID 178490919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxamide (0.9 g) and diethyl carbonate (1.2 mL) in THF (30 mL) was added potassium tert-butoxide (1.2 g). The mixture was refluxed under nitrogen for 6 h. It was then cooled down to room temperature. Water (20 mL) was added and the reaction mixture was concentrated to about 20 mL. It was neutralized with 1N HCl to pH 6 and filtered. Solid was collected and washed with water, and air dried to give desired product. 1H NMR (400 MHz, MeOD-d4) δ 7.24 (d, 2H), 7.21 (m, 1H), 6.92 (d, 2H), 6.88 (m, 1H), 5.52 (s, 2H), 3.78 (s, 3H) ppm; ESMS calculated for C12H11N5O3 (m/z): 273.0, found (M+H+): 274.0.

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 6 h
  2. concentrationthe reaction mixture was concentrated to about 20 mL
  3. filtrationfiltered
  4. customSolid was collected
  5. washwashed with water, and air
  6. customdried

Sources & evidence

ORD record
ord-af8a5b45b24c448f8e74c9098ee76a73
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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