Cyanoacetamide → HCID 13649668, compound

HRID 280657Notes

Reaction equation

HRID 280657 reaction equation
[Na].[C:2]([CH2:4][C:5]([NH2:7])=[O:6])#[N:3].[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[S:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH2:12][N:13]=[N+:14]=[N-:15]>C(O)C>[NH2:3][C:2]1[N:13]([CH2:12][C:11]2[CH:16]=[CH:17][C:18]([S:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:9]([Cl:8])[CH:10]=2)[N:14]=[N:15][C:4]=1[C:5]([NH2:7])=[O:6]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 5360545SodiumHCID 13649677HCID 13649677, compound

Product 1

HCID 13649668HCID 13649668, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of sodium (276 mg, 12.0 mmol) in absolute ethanol (28 ml) at 60° C. was added 2-cyanoacetamide (952 mg, 11.3 mmol). The mixture was stirred 5 minutes, 3-chloro-4-(4-chlorophenylthio)benzyl azide (1.8 g, 5.8 mmol) was added, and the mixture was refluxed for 1 hour. The mixture was cooled to 0° C. and filtered. The solid product was washed with ethanol (2X), water (4X), ethanol (2X), and diethyl ether, and air dried to provide 1.67 g (73%) of 5-amino-1-(3-chloro-4-[4-chlorophenylthio]-benzyl)-1,2,3-triazole-4-carboxamide, m.p. 202°-203.5° C.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. filtrationfiltered
  3. washThe solid product was washed with ethanol (2X), water (4X), ethanol (2X), and diethyl ether, and air
  4. customdried

Sources & evidence

ORD record
ord-46a8974a6e2c49c29b65ef487c363074
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

Loading…