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

HRID 1413106Notes

Reaction equation

HRID 1413106 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[C:8]3[C:13](=[CH:14][C:4]=2[N:3]=1)[CH:12]=[CH:11][CH:10]=[CH:9]3.[SH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.O>C(O)C.[OH-].[Na+]>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][S:15][C:2]1[NH:6][C:5]2[CH:7]=[C:8]3[C:13](=[CH:14][C:4]=2[N:3]=1)[CH:12]=[CH:11][CH:10]=[CH:9]3

Participants

6

Reactant 3

HCID 962WaterHCID 2560712-PyridinemethanethiolHCID 198461182-Chloro-1H-naphtho[2,3-d]imidazole

Product 1

HCID 223941842-[(2-pyridylmethyl)thio]-1H-naphth[2,3-d]imidazoleYield 51.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.92 g of 2-chloro-1H-naphth[2,3-d]imidazole and 0.57 g of 2-mercaptomethylpyridine were heated under reflux for 18 hours in 15 ml of ethanol and 4.5 ml of 1 N caustic soda. 50 ml of water were added to the reaction solution, which was then extracted twice with a total amount of 50 ml of ethyl acetate. The organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate, and evaporated to dryness on a rotary evaporator. Crystallisation from 50 ml of acetonitrile provided 0.68 g of 2-[(2-pyridylmethyl)thio]-1H-naphth[2,3-d]imidazole having a m.p. of 169°-170°.

Workup

  1. extractionwas then extracted twice with a total amount of 50 ml of ethyl acetate
  2. washThe organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness on a rotary evaporator
  5. customCrystallisation from 50 ml of acetonitrile

Sources & evidence

ORD record
ord-d052b7346938488db2cc38944b82d498
Source dataset
uspto-grants-1981_02
Patent number
US04248880

Reaction notes

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