Cyclopropylamine → 4-(Cyclopropylsulfamoyl)benzoic acid

HRID 72954

반응식

HRID 72954 반응식
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH:14]1([NH2:17])[CH2:16][CH2:15]1>ClCCl>[CH:14]1([NH:17][S:2]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH2:16][CH2:15]1

참가 물질

4

반응물 2

HCID 69828CyclopropylamineHCID 823854-(Chlorosulfonyl)benzoic acid

생성물 1

HCID 11341514-(Cyclopropylsulfamoyl)benzoic acid수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 4-chlorosulfonylbenzoic acid (10.0 g, 45.3 mmol) in dichloromethane (350 mL) at 0° C. was added cyclopropanamine (15.5 g, 19 mL, 271.9 mmol). The reaction mixture was allowed to warm to room temperature over 16 hours. The solvent was evaporated under reduced pressure. The residue was dissolved in water (150 mL) and acidified using hydrochloric acid. The aqueous layer was extracted with EtOAc (2×200 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 4-(cyclopropylsulfamoyl)benzoic acid (10.0 g, 92%) as a white solid. ESI-MS m/z calc. 241.0. Found 242.5 (M+1)+; Retention time: 0.84 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.27 (s, 1H), 7.97 (d, J=8.3 Hz, 2H), 7.91 (d, J=2.5 Hz, 1H), 7.75 (d, J=8.3 Hz, 2H), 2.03-1.90 (m, 1H), 0.38-0.28 (m, 2H), 0.23-0.15 (m, 2H).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water (150 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-565b84c7b0b54097a5caefa938cf5259
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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