Sodium Cyanide → 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxamide

HRID 2174289Notes

Reaction equation

HRID 2174289 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15](OCC)=[O:16])=[N:6]1.[C-]#[N:25].[Na+].N.CO>>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]([NH2:25])=[O:16])=[N:6]1

Participants

4

Reactant 3

HCID 8929Sodium CyanideHCID 21705897Ammonia methanolHCID 69093312ethyl 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxylate

Product 1

HCID 690939441-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxamideYield 99%

Procedure

A solution of ethyl 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxylate (Intermediate-3, 0.78 mmol) and sodium cyanide (0.1 equiv) in ammonia/MeOH (7N, 30 equiv, 3.4 mL) in a seal tube was heated at 90° C. for 24 h. The reaction mixture was cooled to room temperature, conc. and dried in vacuo to afford 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxamide as a tan solid (>99% yield).

Workup

  1. customconc. and dried in vacuo

Sources & evidence

ORD record
ord-ebf7ceed4f0345d592c30d524092a007
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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