HCID 13034031, compound → HCID 23303055, compound

HRID 1488986Notes

Reaction equation

HRID 1488986 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) δ8.25 (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) δ166.08, 157.95, 150.34, 148.28, 147.71, 38.31, 128.76, 124.79, 124.58, 122.94, 121.68, 119.49, 13.97, 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-bfa87eb46d6b47cbbbc7d47107485d36
Source dataset
uspto-grants-1997_10
Patent number
US05677302

Reaction notes

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