Cyanamide → HCID 15888355, compound

HRID 1953144Notes

Reaction equation

HRID 1953144 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.[N:18]#CN>ClCCl>[NH2:18][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 9864CyanamideHCID 13034031HCID 13034031, compound

Product 1

HCID 15888355HCID 15888355, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (2.00 g, 8.08 mmole) in 25 mL dichloromethane, cyanamide (0.728 g, 16.2 mmole) was added in one portion and the mixture was stirred for 48 h at room temperature. The resulting precipitate was filtered, slurried in methanol and subsequently washed with dichloromethane to give 1.01 g (66%) of 3-amino-1,2,4-thiadiazolo[4,5-a]benzimidazole as colourless crystals: mp 255-256° C.; 1H NMR (DMSO-d6)δ 8.23 (d, 1H), 7.71 (d, 1H), 7.43 (t, 1H), 7.54 (s, 2H), 7.32 (t, 1H) ppm; IR (KBr)ν 3302, 3151, 1661, 1577, 1487, 1473, 1251, 1207, 810 cm-1 ; HRMS calcd for C8H6N4S 190.0313, found 190.0293. Anal. Calcd for C8H6N4S: C, 50.51;H. 3.18; N. 29.45. Found: C, 50.26;H, 3.26; N, 29.38.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washsubsequently washed with dichloromethane

Sources & evidence

ORD record
ord-f6532b09628f487b8dbe2945ffd1cf1e
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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