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

HRID 277575

반응식

HRID 277575 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 2574763-(Morpholine-4-sulfonyl)benzoic acid수율 81.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d49c8c3249fa4b67942e23d401120cdf
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355633B1

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