Pyridine → HCID 136395932, compound

HRID 1953149Notes

Reaction equation

HRID 1953149 reaction equation
O=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[N:10]2[C:6](=[N:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[S:5][N:4]=1.N1C=CC=CC=1.Cl.[NH2:28][OH:29]>C(O)C>[OH:29][N:28]=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[N:10]2[C:6](=[N:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[S:5][N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 9838563HCID 9838563, compound

Product 1

HCID 136395932HCID 136395932, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.5 g (1.79 mmol) of 3-(oxophenylmethyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole in 7 mL of ethanol was added 0.5 mL (6.46 mmol) of pyridine and 0.5 g (7.20 mmol) of hydroxylamine hydrochloride. The mixture was refluxed for overnight. The precipitate was collected by filtration, and washed with methanol and dichloromethane to give the crude product, which was recrystallized from methanol to yield 0.47 g (89%) of the title compound as white crystals. mp 247° C.; 1H NMR (DMSO-d6)δ 11.89 (s, 1H), 7.81 (d, 1H), 7.73 (dd, 2H), 7.45-7.53 (m, 5H), 7.32 (t, 1H) ppm; 13C NMR (CDCl3)δ 168.25, 155.24, 150.52, 147.95, 136.94, 135.67, 134.30(2C), 133.03, 131.52(2C), 130.35, 127.26, 124.28, 116.91 ppm; IR (KBr)δ 2731, 1549, 1475, 1450, 1251, 1194, 983, 753, 736 cm-1HRMS calcd for C15H10N4OS 294.0575, found 294.0583

Workup

  1. temperatureThe mixture was refluxed for overnight
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with methanol and dichloromethane
  4. customto give the crude product, which
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-cb9722aa76df4937957c0d366c00ea45
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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