Sodium Hydroxide → HCID 23313802, compound

HRID 745585Notes

Reaction equation

HRID 745585 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]3[CH2:12][CH2:11][NH:10][C:8]3=[CH:9][C:4]=2[N:3]=[C:2]1[SH:13].[OH-].[Na+].[ClH:16].[Cl:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>O>[ClH:17].[ClH:16].[ClH:17].[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:13][C:2]1[NH:1][C:5]2[CH:6]=[C:7]3[CH2:12][CH2:11][NH:10][C:8]3=[CH:9][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 178527750HCID 178527750, compound

Product 1

HCID 23313802HCID 23313802, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.5 g of 1,5,6,7-tetrahydropyrrolo-(2,3-f)benzimidazole-2-thiol, suspended in 40 ml of alcohol, were added dropwise while stirring 1.2 g of sodium hydroxide in 20 ml of water and, after 30 minutes, there were added 2.4 g of 2-chloromethyl-pyridine hyrochloride. The mixture was left to boil at reflux overnight, then evaporated and the residue was taken up in methylene chloride. The solution obtained was washed with 100 ml of 3N sodium hydroxide and three times with 100 ml of water, dried over sodium sulfate and evaporated in vacuo. The crude product, dissolved in methanol, was treated with 30 ml of hydrochloric acid in ethyl acetate and the precipitated crystals were removed by filtration under suction. There were obtained 1.6 g (31.3% of theory) of 1,5,6,7-tetrahydro-2-[(2-pyridylmethyl)thio]pyrrolo(2,3-f)benzimidazole trihydrochloride of melting point 207°-209° C.

Workup

  1. additionwere added dropwise
  2. waitThe mixture was left
  3. temperatureat reflux overnight
  4. customevaporated
  5. customThe solution obtained
  6. washwas washed with 100 ml of 3N sodium hydroxide and three times with 100 ml of water
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. dissolutionThe crude product, dissolved in methanol
  10. additionwas treated with 30 ml of hydrochloric acid in ethyl acetate
  11. customthe precipitated crystals were removed by filtration under suction

Sources & evidence

ORD record
ord-3f6f18cb2eca4953878c4e520527b392
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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