Guanidine Hydrochloride → HCID 25178483, compound

HRID 2375280Notes

Reaction equation

HRID 2375280 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH:12]([CH3:14])[CH3:13])[C:10]([CH3:15])=[N:9][CH:8]=1)=O.Cl.[NH2:18][C:19]([NH2:21])=[NH:20].C[O-].[Na+]>C(O)CCC>[NH2:20][C:19]1[N:21]=[C:5]([C:7]2[N:11]([CH:12]([CH3:13])[CH3:14])[C:10]([CH3:15])=[N:9][CH:8]=2)[CH:4]=[CH:3][N:18]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 669246665-(3-Dimethylaminoprop-2-en-1-oyl)-1-isopropyl-2-methylimidazole

Product 1

HCID 25178483HCID 25178483, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-isopropyl-2-methylimidazole (Method 24; 4.9 g, 22.2 mmol) and guanidine hydrochloride (5.3 g, 55.6 mmol) were suspended in 1-butanol (70 ml). NaOMe (4.8 g, 88 mmol) was added in one portion and the mixture heated under reflux, under an atmosphere of nitrogen, for 3 hours. The volatiles were removed by evaporation. Water (50 ml) was added and extracted EtOAc (3×50 ml). The organic layers were combined and dried evaporated in vacuo. The residue triturated with isohexane to give the title compound as a brown solid (1.9 g, 40%). NMR: 1.46 (d, 6H), 2.43 (s, 3H), 5.45 (m, 1H), 6.50 (brs, 1H), 6.74 (d, 1H), 7.28 (s, 1H), 8.12 (d, 1H); m/z 218

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux, under an atmosphere of nitrogen, for 3 hours
  3. customThe volatiles were removed by evaporation
  4. additionWater (50 ml) was added
  5. extractionextracted EtOAc (3×50 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customThe residue triturated with isohexane

Sources & evidence

ORD record
ord-cbbd79d91ab94762801b812b04618917
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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