4-Methoxybenzenesulfonyl chloride → N-(isopropoxy)-4-methoxy-1-benzenesulfonamide

HRID 29150ノート

反応式

HRID 29150 の反応式
[CH:1]([O:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:3])[CH3:2].NN.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C>O1CCCC1.ClCCl>[CH:1]([O:4][NH:5][S:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)(=[O:28])=[O:27])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 27689132-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dione

生成物 1

HCID 22997078N-(isopropoxy)-4-methoxy-1-benzenesulfonamide収率 69%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A vigorously stirred solution of 2-isopropoxy-1H-isoindole-1,3(2H)-dione [2.50 g, 12.2 mmol, Synth. Comm., 22(10), 1427-1432 (1992)] in 35 mL of tetrahydrofuran under an Argon atmosphere at ambient temperature was treated with anhydrous hydrazine (0.421 mL, 13.41 mmol). After 1.5 hours, 4-methoxybenzenesulphonyl chloride (3.024 g, 14.63 mmol), dichloromethane (20 mL) and N,N-diisopropylethylamine (6.38 mL, 36.6 mmol) was added with continued stirring. After an additional 2 hours at ambient temperature, the reaction mixture was evaporated in vacuo to a residue and partitioned between ethyl acetate and 1N hydrochloric acid. The layers were separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with 5% w/v potassium carbonate and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue. The crude material was purified on Flash grade silica gel eluting with 30% ethyl acetate in hexane. Fractions containing the product were combined, evaporated in vacuo, and dried under high vacuum to provide N1-(isopropoxy)-4-methoxy-1-benzenesulfonamide (2.061 g, 69%) as a white solid. H1-NMR (chloroform-D3): 1.22 (d, 6H), 3.92 (s, 3H), 4.27 (m, 1H), 6.70 (s, 1H), 7.05 (d, 2H), 7.90 (d, 2H). MS(ESI): 268 (M+Na).

後処理

  1. waitAfter an additional 2 hours at ambient temperature
  2. customthe reaction mixture was evaporated in vacuo to a residue
  3. custompartitioned between ethyl acetate and 1N hydrochloric acid
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted again with ethyl acetate
  6. washThe combined organic layers were washed with 5% w/v potassium carbonate and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a residue
  10. customThe crude material was purified on Flash grade silica gel eluting with 30% ethyl acetate in hexane
  11. additionFractions containing the product
  12. customevaporated in vacuo
  13. customdried under high vacuum

出典と根拠

ORDレコード
ord-71ef0007f0db434fa3c95d0f6b01b997
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

反応ノート

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