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

HRID 2043211Notes

Reaction equation

HRID 2043211 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 to 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 to reflux for 4 hours. The solvent was removed and the residue was used directly in the next procedure.

Workup

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

Sources & evidence

ORD record
ord-75260c8e42cc47849b44da0fb910127b
Source dataset
uspto-grants-2013_11
Patent number
US08586615B2

Reaction notes

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