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

HRID 968924ノート

反応式

HRID 968924 の反応式
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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 253276CyclopentylidenehydrazineHCID 2756315N-hydroxybenzenecarboximidoyl chloride

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒3 回

実験手順

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-en4-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), 1.85 (m, 2H), 1.8 (m., 2H).

後処理

  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

出典と根拠

ORDレコード
ord-dac470c3724f413db2fe7ee607a1756d
出典データセット
uspto-grants-2007_12
特許番号
US07304162B2

反応ノート

読み込み中…