Ethanol → 3-Aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole ditosylate

HRID 963024

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.C([OH:26])C.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>O>[C:28]1([CH3:38])[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:35])=[O:36])=[CH:32][CH:33]=1.[C:28]1([CH3:38])[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:35])=[O:36])=[CH:32][CH:33]=1.[NH2:9][CH2:10][C:11]1[N:12]([C:13]2[S:17][C:16]([CH2:18][CH3:19])=[CH:15][C:14]=2[C:8](=[O:26])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:20]([CH3:23])=[N:21][N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (702 g) was suspended in a mixed solvent (4.9 l) of ethanol and water (9:1), and p-toluenesulfonic acid monohydrate (1165 g) was added. The mixture was stirred at 80° C. for 1.5 hours. The mixture was concentrated to about 2.5 l by evaporating the solvent under reduced pressure, and ethyl acetate (4 l) was added. The reaction mixture was filtered to give crystals, and the crystals were washed with ethyl acetate and ethanol and dried to give 1214 g of 3-aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole di-p-toluenesulfonate.

Workup

additionwas added
concentrationThe mixture was concentrated to about 2.5 l
customby evaporating the solvent under reduced pressure, and ethyl acetate (4 l)
additionwas added
filtrationThe reaction mixture was filtered
customto give crystals
washthe crystals were washed with ethyl acetate and ethanol
customdried

Sources & evidence

ORD record: ord-c8e5dd973f9a439a90192d3c37e328c6
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760032

Linked notes

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