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

HRID 277580

反応式

HRID 277580 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-73b32ef307804d0996e14009bb4be59c
出典データセット
uspto-grants-2002_03
特許番号
US06355633B1

関連ノート

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