Triethylamine → N'-[5-(2-chloro-benzoyl)-thiazol-2-yl]-N,N-dimethyl-formamidine

HRID 1010546

Reaction equation

HRID 1010546 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].CO[CH:7]([N:10]([CH3:12])[CH3:11])OC.[CH2:13](N(CC)CC)C.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])=[O:23]>CO>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:22]([C:21]1[S:3][C:2]([N:4]=[CH:12][N:10]([CH3:7])[CH3:11])=[N:1][CH:13]=1)=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 2723790ThioureaHCID 27357852-Bromo-2'-chloroacetophenone

Product 1

HCID 66628633N'-[5-(2-chloro-benzoyl)-thiazol-2-yl]-N,N-dimethyl-formamidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of thiourea (4.95 g, 65.0 mmol) and dimethoxymethyl-dimethyl-amine (23.2 g, 195 mmol) in methanol (80 mL) was heated at reflux for 30 minutes. After allowing the mixture to cool, triethylamine (19.8 g, 195 mmol) and a solution of 2-bromo-1-(chloro-phenyl)-ethanone (crude from last step) in methanol (50 mL) were added. The mixture was heated at reflux for 4 hours. The solvent was removed and the residue was used directly in the next procedure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperatureto cool
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 4 hours
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-4e13dbc8740d49a09bb05a10efdbc2ac
Source dataset
uspto-grants-2011_07
Patent number
US07977322B2

Linked notes

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