Pyridine → HCID 19866629, compound

HRID 232084Notes

Reaction equation

HRID 232084 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1N.N([O-])=O.[Na+].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>Cl.O>[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:10][C:2]1[NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 240500869104-73-0HCID 23668193Sodium Nitrite

Product 1

HCID 19866629HCID 19866629, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

2-(1H-Benzimidazol-2-yl thio)benzenamine (8.5 g) in dilute hydrochloric acid (680 ml) was cooled (0° to -5°) with stirring and sodium nitrite (2.68 g) in water (85 ml) was added dropwise, keeping the temperature below 0°. The resulting diazonium salt solution was stirred at 0° for 0.5 hours, then added portionwise to pyridine (800 ml) with stirring at 80° for 1 hour. The pyridine was distilled off, and replaced with 880 ammonia which was in turn distilled off. The residue was treated with water and extracted into dichloromethane, washed, dried, evaporated under reduced pressure and purified by flash column chromatography using dichloromethane:ethyl acetate, 9:2 as eluant to give 3.07 g of the sub-title product.

Workup

  1. customthe temperature below 0°
  2. stirringwith stirring at 80° for 1 hour
  3. distillationThe pyridine was distilled off
  4. distillationdistilled off
  5. additionThe residue was treated with water
  6. extractionextracted into dichloromethane
  7. washwashed
  8. customdried
  9. customevaporated under reduced pressure
  10. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-7cedf2549c1f4ea99fc8af28387b092f
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Reaction notes

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