Pyridine → HCID 15059464, compound

HRID 1199446Notes

Reaction equation

HRID 1199446 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+].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>Cl.O>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[CH:25]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 692784-MethoxypyridineHCID 240500869104-73-0HCID 23668193Sodium Nitrite

Product 1

HCID 15059464HCID 15059464, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To an ice cold solution of 2-(1H-benzimidazol-2-yl thio)benzenamine (1.70 g) in dilute hydrochloric acid (11 ml) was added dropwise a solution of sodium nitrite (0.53 g) in water (5 ml), keeping the temperature below 0°. The reaction mixture was stirred at this temperature for 0.5 hours then added portionwise to a mixture of 4-methoxypyridine (42.40 g) and pyridine (0.57 g) stirring at 80° for 1 hour. The pyridines were distilled off, replaced with 880 ammonia which was in turn distilled off. The residue was treated with water, extracted into dichloromethane, washed, dried, evaporated and the residue was purified by flash column chromatography using ethyl acetate as eluant to give the sub-title product as a creamish foam, 0.20 g.

Workup

  1. customthe temperature below 0°
  2. stirringstirring at 80° for 1 hour
  3. distillationThe pyridines were distilled off
  4. distillationdistilled off
  5. additionThe residue was treated with water
  6. extractionextracted into dichloromethane
  7. washwashed
  8. customdried
  9. customevaporated
  10. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-02f14e07877e45dd844bb180b20ebeee
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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