Water → 3-Amino-6-bromo-5-(trifluoromethyl)pyrazine-2-carbohydrazide

HRID 574201Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:11]([NH2:12])=[N:10][C:9]([C:13]([F:16])([F:15])[F:14])=[C:8]([Br:17])[N:7]=1)=O)C.O.[NH2:19][NH2:20].O>CCO>[NH2:12][C:11]1[C:6]([C:4]([NH:19][NH2:20])=[O:3])=[N:7][C:8]([Br:17])=[C:9]([C:13]([F:16])([F:15])[F:14])[N:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-Amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid ethyl ester (Int. F1) (1.00 g, 3.18 mmol) in dry EtOH (25 ml) was added hydrazine monohydrate (309 ul, 6.37 mmol) and the mixture was stirred at reflux (ca. 90° C.). After 3 hr 45 min the reaction mixture was cooled in an ice bath and added to water. The resulting yellow ppt was filtered under vacuum and dried in a vacuum oven overnight to give the title compound as a yellow solid 1H NMR (400 MHz, DMSO-d6) 610.10 (1H, s), 8.00 (2H, s), 4.65 (2H, s).

Workup

temperatureAfter 3 hr 45 min the reaction mixture was cooled in an ice bath
filtrationThe resulting yellow ppt was filtered under vacuum
customdried in a vacuum oven overnight

Sources & evidence

ORD record: ord-9f026a0d7bf94a2ab5dbeacbcc97861f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034879B2

Reaction notes

Loading…