Hydrochloric Acid → 4-(6-Acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride

HRID 2379848Notes

Reaction equation

HRID 2379848 reaction equation
[ClH:1].[C:2]([NH:5][CH2:6][C:7]1[N:12]=[C:11]([C:13]2[N:14]=[C:15]([N:18]=[C:19]([NH2:21])[NH2:20])[S:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH3:3].C(OC(C)C)(C)C>CO>[ClH:1].[ClH:1].[C:2]([NH:5][CH2:6][C:7]1[N:12]=[C:11]([C:13]2[N:14]=[C:15]([N:18]=[C:19]([NH2:20])[NH2:21])[S:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 104469404-(6-(Acetamidomethyl)pyridin-2-yl)-2-guanidinothiazole

Product 1

HCID 189538284-(6-Acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4N-Dioxanic hydrogen chloride (48.0 ml) was added dropwise to a solution of 4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (18.6 g) in methanol (50 ml) at ambient temperature for 5 minutes. After the mixture was stirred at the same temperature for 30 minutes. To the mixture was added a diisopropyl ether and the isolated precipitate was collected by filtration. The precipitate was recrystallized from a mixture of methanol and diisopropyl ether to give 4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride (16.29 g).

Workup

  1. filtrationthe isolated precipitate was collected by filtration
  2. customThe precipitate was recrystallized from a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-4f8a4d56f670470d83da87686e22c464
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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