Sodium Hydroxide → HCID 13343794, compound

HRID 745579Notes

Reaction equation

HRID 745579 reaction equation
[CH3:1][C:2]1([CH3:15])[O:14][C:5]2=[CH:6][C:7]3[NH:11][C:10]([SH:12])=[N:9][C:8]=3[CH:13]=[C:4]2[O:3]1.[OH-].[Na+].Cl.Cl[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>O>[CH3:1][C:2]1([CH3:15])[O:3][C:4]2=[CH:13][C:8]3[NH:9][C:10]([S:12][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:11][C:7]=3[CH:6]=[C:5]2[O:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 178431158HCID 178431158, compound

Product 1

HCID 13343794HCID 13343794, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4.45 g of 2,2-dimethyl-5H-1,3-dioxolo-(4,5-f)benzimidazole-6-thiol, suspended in 100 ml of alcohol, were added dropwise while stirring 1.63 g of sodium hydroxide in 50 ml of water and, after 30 minutes, there were added 3.4 g of 2-chloromethyl-pyridine hydrochloride. The mixture was left to boil at reflux overnight, then evaporated and the residue was taken up in 500 ml of ethyl acetate. This was washed with 100 ml of 3N sodium hydroxide, three times with 100 ml of water, dried over sodium sulfate and evaporated in vacuo. The crude product was recrystallized from acetonitrile. There were obtained 4.6 g (73.4% of theory) of 2,2-dimethyl-6-[(2-pyridyl-methyl)thio]-5H-1,3-dioxolo(4,5-f)benzimidazole of melting point 210°-211° C.

Workup

  1. additionwere added dropwise
  2. waitThe mixture was left
  3. temperatureat reflux overnight
  4. customevaporated
  5. washThis was washed with 100 ml of 3N sodium hydroxide, three times with 100 ml of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d9eb4d974e61497d837ca1fac1eed96d
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

Loading…