Pyridine → 2-Methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester

HRID 277580

반응식

HRID 277580 반응식
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[S:17](Cl)(=[O:19])=[O:18].N1C=CC=CC=1.O1CCOCC1>C(OCC)(=O)C>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[S:17]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])(=[O:19])=[O:18]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6404Neopentyl alcoholHCID 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 312751,4-Dioxane

생성물 1

HCID 571129482-Methyl-5-nitro-benzenesulfonic acid, 2,2-dimethylpropyl ester수율 57.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Neopentyl alcohol (0.75 g, 8.50 mmol) was added to a solution of commercially available 2-methyl-5-nitro-benzenesulfonyl chloride (1.00 g, 4.20 mmol), pyridine (1.72 mL, 21.2 mmol and anhydrous dioxane (40 mL). A water cooled condenser was attached and the material was heated to reflux. After stirring for two days the mixture was cooled to room temperature and diluted with ethyl acetate (350 mL). The organic layer was washed with water, then 1 N HCl solution, and finally brine. After drying with MgSO4 the solution was concentrated to afford 690 mg of the title compound as a yellow solid.(55%): 1HNMR (DMSO-6) δ8.57 (d, J=2 Hz, 1H), 8.51 (dd, J=8 Hz, 2 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 3.78 (s, 2H), 2.70 (s, 3H), 0.88 (s, 9H); MS (EI): [M+] 287; Anal. Calc. for C12H17NO5S: C, 50.16; H, 5.96; N, 4.88. Found: C, 49.83; H, 5.69; N, 4.90.

후처리

  1. customA water cooled condenser was attached
  2. temperaturethe material was heated to reflux
  3. washThe organic layer was washed with water
  4. dry with materialAfter drying with MgSO4 the solution
  5. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-73b32ef307804d0996e14009bb4be59c
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355633B1

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