Methane → HCID 178508147, compound

HRID 1762117Notes

Reaction equation

HRID 1762117 reaction equation
[NH2:1][C:2]1[C:16]([NH2:17])=[CH:15][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)[NH:8][C:4]=2[CH:3]=1.[N:18]#[C:19]Br.C>>[NH2:18][C:19]1[NH:17][C:16]2[CH:15]=[C:5]3[N:6]=[C:7]([C:9]4[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=4)[NH:8][C:4]3=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 297MethaneHCID 10476Cyanogen BromideHCID 20042452HCID 20042452, compound

Product 1

HCID 178508147HCID 178508147, compound

Procedure

2.9 g. 5,6-diamino-2-(4-pyridyl)-benzimidazole and 1.3 g. cyanogen bromide are stirred for 2 hours at 85° C. with the exclusion of moisture. After cooling to ambient temperature, the reaction mixture is treated with active charcoal, filtered and the filtrate evaporated to dryness. The residue is suspended in water, the pH value is adjusted to 8.5 with aqueous ammonia solution and filtered off with suction. The 1.47 g. of residue obtained is applied to 15 g. silica gel 60 and eluted with a mixture of methylene chloride and ammoniacal methanol (95:5 v/v to 92:8 v/v). The appropriate fractions are evaporated to dryness and the residue is dissolved in methanol. Isopropanol is added thereto until turbid and then left to crystallise. There is obtained 0.52 g. of the desired compound; m.p. >320° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness
  3. filtrationfiltered off with suction
  4. customof residue obtained
  5. washsilica gel 60 and eluted with a mixture of methylene chloride and ammoniacal methanol (95:5 v/v to 92:8 v/v)
  6. customThe appropriate fractions are evaporated to dryness
  7. dissolutionthe residue is dissolved in methanol
  8. additionIsopropanol is added
  9. waituntil turbid and then left
  10. customto crystallise
  11. customThere is obtained 0.52 g

Sources & evidence

ORD record
ord-2cabc4bcf61e4d3eb79df003f3a442fb
Source dataset
uspto-grants-1989_05
Patent number
US04831032

Reaction notes

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