Pyridine → HCID 136395932, compound

HRID 2289602Notes

Reaction equation

HRID 2289602 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-(oxophenyl-methyl)-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) ν 2731, 1549, 1475, 1450, 1251, 1194, 983, 753, 736 cm-1. HRMS 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-62cb79f38fa44c919bed2e2e105d9596
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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