HCID 13034031, compound → HCID 23303055, compound

HRID 1953137Notes

Reaction equation

HRID 1953137 reaction equation
C([N:5]1[C:12](=O)[N:11]2[C:7](=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=32)[S:6]1)CCC.[Br:18][C:19]([Br:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)C#N>ClCCl>[Br:18][C:19]([Br:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[C:12]1[N:11]2[C:7](=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=32)[S:6][N:5]=1

Participants

4

Reactant 2

HCID 13034031HCID 13034031, compoundHCID 23303060HCID 23303060, compound

Product 1

HCID 23303055HCID 23303055, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (2.0 g, 8.1 mmol) and dibromo(2-pyridyl)acetonitrile (4.91 g, 17.8 mmol) in 50 mL of dichloromethane was heated to reflux for 16 h. After cooling to room temperature, the precipitate was filtered, washed with dichloromethane and dried to give 2.76 g (80%) of the title compound as a light-brown solid: mp 195° C. (dec); 1H NMR (CDCl3)δ 8.25 (m, 2H), 7.96 (dt, 1H), 7.76 (d, 1H), 7.32 (m, 2H), 6.95 (t, 1H), 6.92 (s, 1H) ppm; 13C NMR (CDCl3)δ 166.08, 157.95, 150.34, 148.28, 147.71, 138.31, 128.76, 124.79, 124.58, 122.94, 121.68, 119.49, 113.97, 54.37 ppm; HRMS calcd for C14H8Br2N4S: 421.8836, found: 421.8850.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. filtrationthe precipitate was filtered
  4. washwashed with dichloromethane
  5. customdried

Sources & evidence

ORD record
ord-06cd4232a51c4a96a772161bfb507f82
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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