Water → HCID 10778061, compound

HRID 1068568Notes

Reaction equation

HRID 1068568 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18][CH:17]=1.O>CN(C=O)C>[N:16]1([C:2]2[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[CH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 10778061HCID 10778061, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

30.5 g (167 mmol) of 2,4,6-trichloropyrimidine dissolved in DMF (300 ml) was cooled to −5° C., added with potassium carbonate (40 g) and benzimidazole (17.7 g, 150 mmol) and stirred for 30 minutes. The reaction mixture was further stirred at room temperature overnight. The reaction mixture was added with water (500 ml) and the precipitated crystals were collection by filtration. The obtained crude crystals were purified by silica gel chromatography to obtain 12.8 g (yield: 32%) of 2-(benzimidazol-1-yl)-4,6-dichloropyrimidine with melting point of 173° C. -175° C. as colorless crystals.

Workup

  1. stirringThe reaction mixture was further stirred at room temperature overnight
  2. customcollection
  3. filtrationby filtration
  4. customThe obtained crude crystals
  5. customwere purified by silica gel chromatography

Sources & evidence

ORD record
ord-2bc0d0fd0a984ea2a8e741a54df569e6
Source dataset
uspto-grants-2001_06
Patent number
US06251900B1

Reaction notes

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