Guanidine Hydrochloride → 2-[3-Phenylbenzoyl]guanidine hydrochloride

HRID 399865

반응식

HRID 399865 반응식
[ClH:1].[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[C:9]1([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[C:18](OC)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C>CO.O>[ClH:1].[C:9]1([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[C:18]([N:4]=[C:3]([NH2:5])[NH2:2])=[O:19])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

참가 물질

7

반응물 4

HCID 5742Guanidine HydrochlorideHCID 8857Ethyl AcetateHCID 9855857Methyl 3-phenylbenzoateHCID 10942334Sodium Methoxide

생성물 1

HCID 189454072-[3-Phenylbenzoyl]guanidine hydrochloride수율 17.6%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

To a solution of guanidine hydrochloride (2.7 g) in methanol (12 ml) was added sodium methoxide (5.13 g, 28% in methanol) and the mixture was stirred for 15 minutes under nitrogen. To this mixture was added a solution of methyl 3-phenylbenzoate (1.20 g) in methanol (2 ml) and the mixture was stirred for 6 hours. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (50 ml). The organic layer was successively washed with 5N-sodium hydroxide aqueous solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on alumina (100 ml) and eluted with chloroform-methanol (10:1). The fractions containing the desired product were collected and evaporated in vacuo. The residue was crystallized from 4N-hydrogen chloride-ethyl acetate. The crystalline was recrystallized from ethanol to afford 2-[3-phenylbenzoyl]guanidine hydrochloride (274.0 mg).

후처리

  1. stirringthe mixture was stirred for 6 hours
  2. washThe organic layer was successively washed with 5N-sodium hydroxide aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on alumina (100 ml)
  6. washeluted with chloroform-methanol (10:1)
  7. additionThe fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo
  10. customThe residue was crystallized from 4N-hydrogen chloride-ethyl acetate
  11. customThe crystalline was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-0e2f8d909e844621b2cc05d5ca6ce18e
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05824691

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