Hydrochloric Acid → N-(4-(2-(4-((amino(imino)methyl)amino)phenyl)ethyl)-1,3-thiazol-2-yl)acetamide

HRID 2117834Notes

Reaction equation

HRID 2117834 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+].[N:25]#[C:26][NH2:27]>C(O)C.C(OCC)(=O)C>[NH2:27][C:26]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1)=[NH:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 516892Sodium BicarbonateHCID 21914814N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamide

Product 1

HCID 178474442N-(4-(2-(4-((amino(imino)methyl)amino)phenyl)ethyl)-1,3-thiazol-2-yl)acetamideYield 59.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of N-(4-(2-(4-aminophenyl)ethyl)-1,3-thiazol-2-yl)acetamide (26 g) in ethanol (500 ml) was added 4N hydrogen chloride in ethyl acetate (25 ml) and cyanamide (6.3 g). The mixture was refluxed for 26 hours. The reaction mixture was cooled to ambient temperature and poured into a mixture of ethyl acetate (500 ml) and saturated sodium hydrogen carbonate solution (500 ml). The resulted precipitate was collected by filtration and washed with water (300 ml) and ethanol (300 ml) to give N-{4-[2-(4-{[amino(imino)methyl]-amino}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide (18 g) as white crystals.

Workup

  1. temperatureThe mixture was refluxed for 26 hours
  2. filtrationThe resulted precipitate was collected by filtration
  3. washwashed with water (300 ml) and ethanol (300 ml)

Sources & evidence

ORD record
ord-b02149b5223b40a2bbd2ff1d0750bcf8
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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