Morpholine → 3-(Morpholine-4-sulfonyl)benzoic acid

HRID 277575

反応式

HRID 277575 の反応式
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>ClCCl>[N:23]1([S:2]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

参加物

5

反応物 3

HCID 8083MorpholineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 81531Diisopropylethylamine

生成物 1

HCID 2574763-(Morpholine-4-sulfonyl)benzoic acid収率 81.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Commercially available 3-(chlorosulfonyl)benzoic acid (3 g, 13.5 mmol) was suspended in dichloromethane (50 mL). Diisopropylethylamine (5.19 mL, 30 mmol) and morpholine (1.67 mL, 21 mmol) were added slowly. After 2 h, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with 3N HCl three times. The ethyl acetate phase was dried over magnesium sulfate and the solvent was removed under reduced pressure, to provide the title product (2.97 g, 81%) as a white solid. 1HNMR (DMSO-d6) δ8.28 (d, J=8 Hz, 1H), 8.20 (s, 1H), 8.01 (d, 8 Hz, 1H), 7.83 (t, J=8 Hz, 1H), 3.91(m, 4H), 3.12 (M, 4H). MS (EI-NEG):[M+] 270.

後処理

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 3N HCl three times
  4. dry with materialThe ethyl acetate phase was dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-d49c8c3249fa4b67942e23d401120cdf
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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