Sodium Hydroxide → HCID 13343802, compound

HRID 745590Notes

Reaction equation

HRID 745590 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]3[O:13][CH2:12][CH2:11][O:10][C:8]3=[CH:9][C:4]=2[N:3]=[C:2]1[SH:14].[OH-].[Na+].Cl.Cl[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>O>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][S:14][C:2]1[NH:3][C:4]2[CH:9]=[C:8]3[O:10][CH2:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[N:1]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 178527752HCID 178527752, compound

Product 1

HCID 13343802HCID 13343802, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4.6 g of 6,7-dihydro-1H-p-dioxino(2,3-f)benzimidazole-2-thiol, suspended in 50 ml of alcohol, were added dropwise while stirring 1.8 g of sodium hydroxide in 25 ml of water and, after 30 minutes, there were added 3.7 g of 2-chloromethyl-pyridine hydrochloride. The mixture was left to boil at reflux overnight, it was then evaporated, and the residue was taken up in methylene chloride. This mixture was washed first with 3N sodium hydroxide, then neutral with water, dried over sodium sulfate and evaporated in vacuo. The crude product was recrystallized from ethyl acetate/petroleum ether. 3.5 g (53% of theory) of 6,7-dihydro-2-[(2-pyridylmethyl)thio]-1H-p-dioxino(2,3-f)benzimidazole of melting point 155°-156° C. were prepared.

Workup

  1. additionwere added dropwise
  2. waitThe mixture was left
  3. temperatureat reflux overnight
  4. customit was then evaporated
  5. washThis mixture was washed first with 3N sodium hydroxide
  6. dry with materialneutral with water, dried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe crude product was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-48a48a4ddcf94983ad47b88c547261e2
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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