Sodium Hydroxide → 2-[(2-pyridylmethyl)thio]-1H-naphth[2,3-d]imidazole

HRID 1413105Notes

Reaction equation

HRID 1413105 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[N:3]=[C:2]1[SH:14])[CH:11]=[CH:10][CH:9]=[CH:8]3.[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:13]=[C:12]3[C:7](=[CH:6][C:5]=2[N:1]=1)[CH:8]=[CH:9][CH:10]=[CH:11]3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 1785277551H-benzo[f]benzimidazole-2-thiol

Product 1

HCID 223941842-[(2-pyridylmethyl)thio]-1H-naphth[2,3-d]imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.1 g of 1H-naphth[2,3-d]imidazole-2-thiol are suspended in 100 ml of alcohol in a 250 ml volume sulphonating flask equipped with a stirrer, thermometer, cooler and dropping funnel. A solution of 4.0 g of sodium hydroxide in 50 ml of water was then added dropwise, and a clear solution formed. The solution was then heated to boiling, 8.2 g of 2-chloromethyl-pyridine-hydrochloride were added, and the resulting mixture was boiled under reflux overnight. The reaction mixture was then concentrated by evaporation, the residue was taken up in 600 ml of ethyl acetate and 200 ml of water, and the ethyl acetate phase was washed twice with 200 ml of water, dried over sodium sulphate, and concentrated by evaporation in vacuo. The residue was recrystallised once from ethyl acetate/petroleum ether and provided 2-[(2-pyridylmethyl)thio]-1H-naphth[2,3-d]imidazole having a melting point of 165°-167°; the hydrochloride melts at 230°-231°.

Workup

  1. customequipped with a stirrer
  2. customa clear solution formed
  3. temperatureThe solution was then heated
  4. temperatureunder reflux overnight
  5. concentrationThe reaction mixture was then concentrated by evaporation
  6. wash200 ml of water, and the ethyl acetate phase was washed twice with 200 ml of water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation in vacuo
  9. customThe residue was recrystallised once from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-09ae89d4a3474830aa0388c9c8e703ed
Source dataset
uspto-grants-1981_02
Patent number
US04248880

Reaction notes

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