Acetic Acid → HCID 19005926, compound

HRID 1743004Notes

Reaction equation

HRID 1743004 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[C:16]([C:18]([NH:20][NH2:21])=[O:19])[N:15]=[N:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]([O-])=O.[Na+].CC(O)=O.C([O-])(O)=O.[Na+]>O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[C:16]([C:18]([N:20]=[N+:21]=[N-:22])=[O:19])[N:15]=[N:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 19005925HCID 19005925, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19005926HCID 19005926, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

N-benzyl-3-(4-hydrazinocarbonyl-1,2,3-triazol -1-yl)pyrrolidine (3.6 g, 0.0125 mol) was dissolved in hot water (40 ml) and then cooled to 0° C. To the cooled suspension NaNO2 (950 mg, 0.0137 mol in 3 ml of water) was added dropwise and then glacial AcOH (7 ml) was added to the reaction mixture was stirred at 0° C. for 15 min. Reaction mixture was then neutralized by the addition of saturated NaHCO3. The separated white solid was filtered and washed with water, dried in vacuum oven. Yield: 3.73 g (100%), m.p. 160° C. 1H NMR (CDCl3) δ: 1.95-2.15 (m, 1H), 2.37-2.83 (m, 3H), 2.94-3.22 (m, 2H), 3.70 (d, 2H), 5.75-5.87 (m, 1H), 7.30 (s, 5H), 8.47 (s, 1H).

Workup

  1. customReaction mixture
  2. filtrationThe separated white solid was filtered
  3. washwashed with water
  4. customdried in vacuum oven

Sources & evidence

ORD record
ord-d7ab527772024197b50f69657fbda410
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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