Hydrochloric Acid → HCID 18953880, compound

HRID 1491846Notes

Reaction equation

HRID 1491846 reaction equation
C([NH:4][CH2:5][C:6]1[S:7][C:8]([C:11]2[N:12]=[C:13]([N:16]=[C:17]([NH2:19])[NH2:18])[S:14][CH:15]=2)=[CH:9][N:10]=1)(=O)C.Cl>C(O)C>[NH2:4][CH2:5][C:6]1[S:7][C:8]([C:11]2[N:12]=[C:13]([N:16]=[C:17]([NH2:19])[NH2:18])[S:14][CH:15]=2)=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11779338HCID 11779338, compound

Product 1

HCID 18953880HCID 18953880, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(2-acetylaminomethylthiazol-5-yl)-2-(diaminomethyleneamino)thiazole (1.46 g) and concentrated hydrochloric acid (2.18 ml) in ethanol (15 ml) was refluxed for 5 hours with stirring. The solvent was evaporated in vacuo. The residue was made basic to pH 10 with 20% aqueous potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was dried over magnesium sulfate and evaporated in vacuo to give 4-(2-aminomethylthiazol-5-yl)-2-(diaminomethyleneamino)thiazole. 1N-hydrochloric acid (4 ml) and then potassium cyanate (360 mg) was added to the suspension of the above residue in water (10 ml) and the mixture was stirred for two hours at ambient temperature, The reaction mixture was alkalized to pH 10 with 20% aqueous potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was dried over magnesium sulfate and evaporated in vacuo. The obtained free base was converted to the dihydrochloride in an usual manner, and which was recrystallized from a mixture of methanol, water and tetrahydrofuran to give 2-(diamino-methyleneamino)-4-(2-ureidomethylthiazol-5-yl)thiazole dihydrochloride (0.65 g).

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-9bb31a780c0d485d9886aa2b83a28114
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

Loading…