Guanidine Hydrochloride → HCID 178425396, compound

HRID 2211186Notes

Reaction equation

HRID 2211186 reaction equation
CC(C)([O-])C.[K+].Cl.[NH2:8][C:9]([NH2:11])=[NH:10].[Cl:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]([Cl:20])[C:14]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[O:29][C:30](S(C)=O)=[N:31][N:32]=1>C(O)(C)(C)C>[ClH:12].[Cl:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]([Cl:20])[C:14]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[O:29][C:30]([NH:10][C:9]([NH2:11])=[NH:8])=[N:31][N:32]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 19375714HCID 19375714, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 178425396HCID 178425396, compoundYield 141.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of potassium tert-butoxide (111.3 mg, 0.99 mmoles) in 15 ml of tert-butyl alcohol is added guanidine hydrochloride (108.2 mg, 1.13 mmoles). The reaction mixture is stirred at room temperature for 10 minutes, then 2,6-dichloro-3-methyl-N-[2-[5-(methylsulfinyl)-1,3,4-oxadiazol-2-yl]phenyl]benzenamine (201.0 mg, 0.526 mmoles) is added, and the reaction mixture is heated at reflux for five minutes. The mixture is concentrated in vacuo. 20 ml of methanol is added to the residue followed by 100 ml of water. The resultant solid is collected by filtration and dissolved in 10% methanol in ethyl acetate. 50 ml of ether is added, followed by a few drops of saturated etheral hydrochloric acid. The white solid is collected and washed with ether to provide 154.4 mg (71%) of 5-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-1,3,4-oxadiazol-2-yl-guanidine monohydrochloride, mp 245°-248° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for five minutes
  3. concentrationThe mixture is concentrated in vacuo
  4. addition20 ml of methanol is added to the residue
  5. filtrationThe resultant solid is collected by filtration
  6. dissolutiondissolved in 10% methanol in ethyl acetate
  7. addition50 ml of ether is added
  8. customThe white solid is collected
  9. washwashed with ether

Sources & evidence

ORD record
ord-01760b4a895c479190098f6e8caa01ff
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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