Hydrochloric Acid → HCID 178512597, compound

HRID 1581137Notes

Reaction equation

HRID 1581137 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[C:12]([NH:14][C:15]([NH2:17])=[NH:16])#N.Cl.[OH-].[Na+]>>[NH:14]([C:12]1[NH:11][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=2[N:10]=1)[C:15]([NH2:17])=[NH:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 51117914-Nitro-1,2-phenylenediamineHCID 178418324HCID 178418324, compound

Product 1

HCID 178512597HCID 178512597, compoundYield 20%

Procedure

A mixture of 4-nitro-o-phenylenediamine (15.3g 0.1 mol), cyanoguanidine (9.25g 0.11 mol) and dilute hydrochloric acid (40 ml, 0.2 mol) was heated under reflux for 11/2 hours. The reaction mixture was cooled, basified with dilute sodium hydroxide, and filtered. The resulting solid was washed well with water (ca 500 ml), dried in vacuo and boiled with ethanol to yield 2-guanidino-5-nitrobenzimidazole (3.90g; 20%) as pale yellow microcrystals m.p. 305°-307°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 11/2 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washThe resulting solid was washed well with water (ca 500 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d6287daa3343452b905bf37c02e3eca1
Source dataset
uspto-grants-1976_01
Patent number
US03935314

Reaction notes

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