Amidinothiourea → HCID 19439682, compound

HRID 1734025Notes

Reaction equation

HRID 1734025 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[C:7]([CH3:16])[CH:6]=1)=O.[NH2:17][C:18](=[N:20][C:21]([NH2:23])=[S:22])[NH2:19]>C(O)C>[NH2:17][C:18](=[N:20][C:21]1[S:22][CH:2]=[C:3]([C:5]2[CH:15]=[CH:14][C:8]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[C:7]([CH3:16])[CH:6]=2)[N:23]=1)[NH2:19]

Participants

4

Reactant 2

HCID 2724563AmidinothioureaHCID 19439696HCID 19439696, compound

Product 1

HCID 19439682HCID 19439682, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(4-chloroacetyl-2-methylbenzyl)acetamide (3.6 g) and (diaminomethylene)thiourea (2.3 g) in ethanol (100 ml) was refluxed for 2 hours under stirring. The reaction mixture was evaporated in vacuo and the residue was suspended in water and resultant mixture was adjusted to pH 8.0 with 20% potassium carbonate aqueous solution and the precipitate was collected by filtration. The precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran, washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from ethanol to give 2-(diaminomethyleneamino)-4-(4-acetylaminomethyl-3-methylphenyl)thiazole (3.15 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. filtrationthe precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-148c0823570041e1b425cd23e24f9392
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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