Sodium Hydroxide → HCID 13961160, compound

HRID 414186Notes

Reaction equation

HRID 414186 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[SH:12][C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[OH-].[Na+]>C(O)C.O>[N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[NH:4][C:3]=1[CH2:2][S:12][C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 785712-ChloromethylbenzimidazoleHCID 178418793HCID 178418793, compound

Product 1

HCID 13961160HCID 13961160, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10.0 g (0.06 mole) of 2-chloromethylbenzimidazole are added to a solution of 6.7 g (0.06 mole) of 2-mercaptopyrimidine and 2.4 g (0.06 mole) of sodium hydroxide in 200 ml of ethanol and 20 ml of water. The mixture is maintained under reflux for 2 hours and the ethanol evaporated off. The residue is taken up with water (50 ml) and extracted with ethyl acetate (3×50 ml), the organic phase is dried with sodium sulfate, filtered and evaporated to a volume of 40 ml of solution, in which there crystallize 10.2 g (70%) of 2-(2-benzimidazolylmethylthio)pyrimidine, melting point 154°-155° C.

Workup

  1. temperatureThe mixture is maintained
  2. temperatureunder reflux for 2 hours
  3. customthe ethanol evaporated off
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. dry with materialthe organic phase is dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated to a volume of 40 ml of solution, in which there
  8. customcrystallize 10.2 g (70%) of 2-(2-benzimidazolylmethylthio)pyrimidine, melting point 154°-155° C.

Sources & evidence

ORD record
ord-e8be11a88e004bd3aa30b60b08b15092
Source dataset
uspto-grants-1988_12
Patent number
US04791114

Reaction notes

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