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

HRID 1855216Notes

Reaction equation

HRID 1855216 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-38a593151b9b4a509ebb072112fa2634
Source dataset
uspto-grants-2015_02
Patent number
US08962856B2

Reaction notes

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