Ammonia → 1-amino-3-(1H-1,2,3-triazol-1-yl)propan-2-ol

HRID 481052Notes

Reaction equation

HRID 481052 reaction equation
Cl[CH2:2][CH:3]([OH:10])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[N:6]1.[NH3:11]>CO>[NH2:11][CH2:2][CH:3]([OH:10])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[N:6]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 187656811-Chloro-3(1,2,3)triazol-1-ylpropan-2-ol

Product 1

HCID 187656671-amino-3-(1H-1,2,3-triazol-1-yl)propan-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Chloro-3(1,2,3)triazol-1-ylpropan-2-ol (2.3 g, 13 mmol) was treated with the solution of NH3 in methanol (25% by weight, 20 mL) at 60° C. overnight in a sealed pressure vessel. After cooling to room temperature, nitrogen was bulbbed into the reaction mixture to remove the ammonia. Evaporation of solvent gave the hydrogen chloride salt of 1-amino-3-(1,2,3)triazol-1-ylpropan-2-ol (2.57 g, 100%). 1H NMR (DMSO-d6) δ2.68 (dd, J=8.8, 12.8 Hz, 1H), 2.97 (dd, J=3.6, 12.8 Hz, 1H), 4.15 (m, 1H), 4.44 (dd, J=6.4, 14 Hz, 1H), 4.57 (dd, J=4.6, 14 Hz, 1H), 5.95 (d, J=5.2 Hz, 1H, OH), 7.77 (s, 1H), 8.01 (brs., 3H, NH3+), 8.12 (s, 1H). MS (m/z) 143.1 (M+1).

Workup

  1. customto remove the ammonia
  2. customEvaporation of solvent

Sources & evidence

ORD record
ord-e2c1cfda807247e89b5a2b51eb176076
Source dataset
uspto-grants-2003_11
Patent number
US06653308B2

Reaction notes

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