Potassium Carbonate → HCID 23536788, compound

HRID 1815894Notes

Reaction equation

HRID 1815894 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[O:15]=[C:16]1[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:19]2[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=2[NH:17]1>C(C#N)(C)=O>[C:24]([O:23][C:21]([N:20]1[C:19]2[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=2[N:17]([C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)[C:16]1=[O:15])=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178102,4-Dichloro-1,3,5-triazineHCID 2756037tert-Butyl 2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate

Product 1

HCID 23536788HCID 23536788, compound

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

3-(4-Chloro-[1,3,5]triazin-2-yl)-2-oxo-2,3-dihydro-benzimidazole-1-carboxylic acid tert-butyl ester was prepared by a process similar to that described by N. A. Meanwell, et al., J. Org Chem., 60,1565-82 (1995). A mixture of 2,4-dichloro-1,3,5-triazine (0.64, 4.26 mmol) and solid K2CO3 (0.6 g, 4.34 mmol) was suspended in AcCN (10 mL) under nitrogen at RT followed by addition of 2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (1.0 g, 4.26 mmol). The mixture was stirred at RT for 1.5 h. The mixture was poured onto ice/water and the white solid formed, was collected by suction filtration and dried under vacuum to give 3-(4-chloro-[1,3,5]triazin-2-yl)-2-oxo-2,3-dihydro-benzimidazole-1-carboxylic acid tert-butyl ester.

Workup

  1. custom3-(4-Chloro-[1,3,5]triazin-2-yl)-2-oxo-2,3-dihydro-benzimidazole-1-carboxylic acid tert-butyl ester was prepared by a process similar to
  2. additionThe mixture was poured onto ice/water
  3. customthe white solid formed
  4. filtrationwas collected by suction filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e38b71d4b5ae4a99b34d6253e85b59a1
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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