Acetic Anhydride → 4-(6-(Acetamidomethyl)pyridin-2-yl)-2-guanidinothiazole

HRID 2379833Notes

Reaction equation

HRID 2379833 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[N:17]=[C:18]([N:21]=[C:22]([NH2:24])[NH2:23])[S:19][CH:20]=2)[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[C:5]([NH:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[N:17]=[C:18]([N:21]=[C:22]([NH2:24])[NH2:23])[S:19][CH:20]=2)[CH:13]=[CH:12][CH:11]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 103997684-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 104469404-(6-(Acetamidomethyl)pyridin-2-yl)-2-guanidinothiazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride was added dropwise to a solution of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.44 g) in pyridine (4.4 ml). After being stirred for two hours at ambient temperature, the mixture was mixed with aqueous potassium carbonate and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo to give 4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole. The residue was converted to the hydrochloride in a usual manner and the salt was recrystallized from a mixture of methanol and diisopropyl ether to give 4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride (0.43 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-9963a6dd4d8a4b4fb7161ccf1b148112
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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