4-Toluenesulfonyl chloride → 6,6-Dimethyl-2-nitro-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine

HRID 1022239노트

반응식

HRID 1022239 반응식
O[CH2:2][C:3]1[N:7]([CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])[N:6]=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.[H-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:10][C:9]1([CH3:12])[O:11][CH2:2][C:3]2=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[N:6][N:7]2[CH2:8]1

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866840171-(5-(Hydroxymethyl)-3-nitro-1H-pyrazol-1-yl)-2-methylpropan-2-ol

생성물 1

HCID 866840186,6-Dimethyl-2-nitro-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine수율 22.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 330e (1.1 g, 5.1 mmol) in DMF (10 mL), was added NaH (60 percent dispersion in mineral oil, 246 mg, 6.14 mmol) at 0° C. The resulting suspension was stirred for 30 min, followed by the addition of p-toluenesulfonyl chloride (1169 mg, 6.14 mmol). The mixture was stirred at 60° C. overnight. After cooling to room temperature, saturated ammonium chloride solution was added and the mixture was extracted with dichloromethane. The combined organic layer was washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate gradient (9:1 to 2:1) to afford 330f (228 mg, 22%). MS-ESI: [M+H]+ 198.3

후처리

  1. stirringThe mixture was stirred at 60° C. overnight
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography
  7. washeluting with petroleum ether/ethyl acetate gradient (9:1 to 2:1)

출처 및 근거

ORD 기록
ord-ef9c36aef1bb40ca8be375b3f3e5ed30
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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