Sodium Hydroxide → HCID 178423989, compound

HRID 1581138Notes

Reaction equation

HRID 1581138 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[C:2]=1[NH2:8].[C:10]([NH:12][C:13]([NH2:15])=[NH:14])#N.[OH-].[Na+]>>[NH:12]([C:10]1[NH:8][C:2]2[C:1]([CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=2[N:7]=1)[C:13]([NH2:15])=[NH:14]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 175932,3-DiaminotolueneHCID 178418324HCID 178418324, compound

Product 1

HCID 178423989HCID 178423989, compoundYield 132.4%

Procedure

A mixture of 2,3-toluenediamine (12.45g, 0.102 mol)(5N HCl 40. 8ml, 0.204 mol) and cyanoguanidine (8.60g, 0.102 mol) was heated on a steam bath for 1 hour. The hot solution was then basified with 40% sodium hydroxide and allowed to cool. The resulting gummy material which separated was extracted into ether. The combined ether extracts were dried (Na2SO4) and treated with ethereal hydrogen chloride to give a pink precipitate (25.55g) m.p. 213°-222°C. This crude product was recrystallised from ethanol/ether. A first crop (14.90g), m.p. 236°-238°C. which contained some unreacted 2,2-toluenediamine was obtained but a second crop (5.00g) of colourless microcrystals m.p. 249°-250°C crystallised as pure 2-guanidino-4-methylbenzimidazole dihydrochloride monohydrate.

Workup

  1. temperaturewas heated on a steam bath for 1 hour
  2. temperatureto cool
  3. customThe resulting gummy material which separated
  4. extractionwas extracted into ether
  5. dry with materialThe combined ether extracts were dried (Na2SO4)
  6. additiontreated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-6f9e655f696946d3833b00d76e71fb68
Source dataset
uspto-grants-1976_01
Patent number
US03935314

Reaction notes

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