Lithium hydroxide, monohydrate → 2,6-DIAMINO-3-(2,3,5-TRICHLOROPHENYL)-PYRAZINE

HRID 392856Notes

Reaction equation

O.[OH-].[Li+].Br.[C:5]([CH:7]([NH:17][CH2:18][C:19]([NH2:21])=[NH:20])[C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:9]=1[Cl:16])#[N:6]>CO>[NH2:6][C:5]1[C:7]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:9]=2[Cl:16])=[N:17][CH:18]=[C:19]([NH2:21])[N:20]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Lithium hydroxide monohydrate (2.9 kg) was stirred in methanol (269 kg) for 60 minutes at 20° C. and then cooled to −10C. 2-{[Cyano-(2,3,5-trichlorophenyl)-methyl]-amino}-acetamidine hydrobromide was added in one portion and the resultant mixture stirred vigorously with cooling at −10° C. Compressed air was gassed over the surface of the reaction for at least 6 hours. The mixture was warmed to 25° C. and concentrated to 3 volumes under vacuum. Water (289 kg) was added over at least 1 hour with stirring. The product was isolated by filtration and the cake washed with water (51 kg) and dried in vacuo at 40° C. Yield 12 Kg (91%). HPLC retention time 11.9 minutes.

Workup

temperaturecooled to −10C
customCompressed air was gassed over the surface of the reaction for at least 6 hours
temperatureThe mixture was warmed to 25° C.
concentrationconcentrated to 3 volumes under vacuum
additionWater (289 kg) was added over at least 1 hour
customThe product was isolated by filtration
washthe cake washed with water (51 kg)
customdried in vacuo at 40° C

Sources & evidence

ORD record: ord-1902f381ba6c4294bf5abcd64ece782a
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803464B2

Reaction notes

Loading…