Cyclopropylamine → 4-(Cyclopropylsulfamoyl)benzoic acid

HRID 72954

反応式

HRID 72954 の反応式
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

参加物

4

反応物 2

HCID 69828CyclopropylamineHCID 823854-(Chlorosulfonyl)benzoic acid

生成物 1

HCID 11341514-(Cyclopropylsulfamoyl)benzoic acid収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-565b84c7b0b54097a5caefa938cf5259
出典データセット
uspto-grants-2014_09
特許番号
US08828996B2

関連ノート

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