Pyrrolidine → HCID 178456693, compound

HRID 617014Notes

Reaction equation

HRID 617014 reaction equation
C([O:3][C:4]([NH:6][N:7]([CH:10]([CH3:12])[CH3:11])[C:8]#[N:9])=O)C.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH:10]([N:7]1[C:8]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:9][C:4]([OH:3])=[N:6]1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 19390523HCID 19390523, compound

Product 1

HCID 178456693HCID 178456693, compoundYield 70%

Conditions

Temperature
30 °C

Procedure

26,6 g (0,15 mole) of 2-isopropyl-2-cyanohydrazinecarboxylic acid ethyl ester is added dropwise to 100 ml of pyrrolidine. The temperature raises to 30° C during the dropwise addition. The whole mixture is then stirred for 12 hours at room temperature and subsequently for 1 hour at 70° C. Then excess pyrrolidine is distilled off in vacuo. To the crystalline residue ethyl acetate is added and the crystals are filtered with suction. There is obtained 21,6 g (70% of theory) of 1-isopropyl-3-hydroxy-5-pyrrolidino-1,2,4-triazole, mp. 123°-125° C.

Workup

  1. distillationThen excess pyrrolidine is distilled off in vacuo
  2. additionTo the crystalline residue ethyl acetate is added
  3. filtrationthe crystals are filtered with suction

Sources & evidence

ORD record
ord-44062f9a01ad43dc9835a5d723b3fded
Source dataset
uspto-grants-1978_02
Patent number
US04076938

Reaction notes

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