Potassium Carbonate → 3-Phenyl-1-oxa-2,4-diaza-spiro[4.4]non-2-en4-ylamine

HRID 339453노트

반응식

HRID 339453 반응식
C([O-])([O-])=O.[K+].[K+].[C:7]1(=[N:12][NH2:13])[CH2:11][CH2:10][CH2:9][CH2:8]1.[C:14](Cl)(=[N:21][OH:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.C(Cl)Cl>[C:15]1([C:14]2[N:12]([NH2:13])[C:7]3([CH2:11][CH2:10][CH2:9][CH2:8]3)[O:22][N:21]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 253276CyclopentylidenehydrazineHCID 2756315N-hydroxybenzenecarboximidoyl chloride

생성물 1

HCID 146846683-Phenyl-1-oxa-2,4-diaza-spiro[4.4]non-2-en4-ylamine수율 50,341.301%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매3회

실험 절차

A round bottom flask was charged with a solution of 20 g of K2CO3 in 50 mL of water and cooled in an ice bath. Cyclopentylidene-hydrazine (7.9 g, 80 mmol) in 25 mL of CH2Cl2 was added, followed by a drop-wise addition of benzohydroximoyl chloride (5 g, 0.032 mmol) in 25 mL of CH2Cl2 over a period of 15 minutes. The mixture was stirred for several days, and allowed to warm to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added and the phases were separated. The organic layer was washed twice with 50 mL of water, dried over MgSO4, and filtered. The solvent was removed in vacuo, leaving 9 g of a waxy solid. Crystallization from ethyl acetate/hexane provided 3.5 g (50%) of 3-phenyl-1-oxa-2,4-diaza-spiro[4.4]non-2-en-4-ylamine after drying. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.72 ((m, 2H), 7.46 (m, 3H), 3.54 (s, 2H), 2.1 (m, 2H), 2.0 (m, 2H), 1.85 (m, 2H), 1.8 (m, 2H).

후처리

  1. temperaturecooled in an ice bath
  2. customthe phases were separated
  3. washThe organic layer was washed twice with 50 mL of water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customleaving 9 g of a waxy solid
  8. customCrystallization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-aa85f187389c4223a8f6207ebd40a343
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895306B2

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