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

HRID 877598

반응식

HRID 877598 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].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[O:17]1[CH2:18][CH2:19][N:14]([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])[CH2:15][CH2:16]1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

생성물 1

HCID 2574763-(Morpholine-4-sulfonyl)benzoic acid수율 52.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-(Chlorosulfonyl)benzoic acid (250 mg, 1.133 mmol) was added to morpholine (99 mg, 1.133 mmol) in the presence of potassium carbonate (313 mg, 2.266 mmol) in THF (5 mL) at room temperature, and reaction mixture allowed to stirred for 12 h at rt. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum, and then compound was purified by column chromatography (3% CH3OH/CH2Cl2) affording the title compound (160 mg) as a solid. 1H NMR (400 MHz, CD3OD): δ 8.34 (m, 1H), 8.32 (d, 1H, J=8.0 Hz), 7.99 (m, 1H), 7.76 (t, 1H, J=8.0 Hz), 3.70 (m, 4H), 2.98 (m, 4H). ESI-MS: 272.0 [M+H]+.

후처리

  1. customreaction mixture
  2. customAfter completion of the reaction
  3. customthe solvent was removed by vacuum
  4. customcompound was purified by column chromatography (3% CH3OH/CH2Cl2)

출처 및 근거

ORD 기록
ord-ecaec209cb1f4c859c0307cebaa5c84c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987335B2

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