P-Toluenesulfonamide → N-(2-Hydroxy-2-(4-nitrophenyl)ethyl)-4-methylbenzenesulfonamide

HRID 1473103

反応式

HRID 1473103 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:23][O:22]2)=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1>[OH:22][CH:21]([C:18]1[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=1)[CH2:23][NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9]

参加物

7

反応物 4

HCID 6269P-ToluenesulfonamideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 922282-(4-Nitrophenyl)oxirane

生成物 1

HCID 68282567N-(2-Hydroxy-2-(4-nitrophenyl)ethyl)-4-methylbenzenesulfonamide

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

Tosylamide (0.69 g, 4.0 mmol), 2-(4-nitrophenyl)oxirane (I83) (0.33 g, 2.0 mmol), benzyltriethylammonium chloride (46 mg, 0.20 mmol) and potassium carbonate (28 mg, 0.20 mmol) were suspended in dioxane (1.0 mL) and the resulting mixture was stirred at 90° C. After four hours the mixture was cooled to room temperature and poured into DCM (15 mL). The resulting mixture was filtered and evaporated. The residue was chromatographed (Isolera, 40 g silica cartridge, 0-100% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I84) as an orange solid (363 mg, 38% yield); 1H NMR (400 MHz, d6-DMSO) δ 8.19-8.13 (m, 2H), 7.64-7.59 (m, 2H), 7.57-7.52 (m, 2H), 7.34 (d, J=7.9 Hz, 2H), 7.27 (s, 1H), 5.82 (d, J=4.5 Hz, 1H), 4.71 (dd, J=10.7, 6.0 Hz, 1H), 2.92 (td, J=6.2, 1.7 Hz, 2H), 2.36 (s, 3H).

後処理

  1. temperatureAfter four hours the mixture was cooled to room temperature
  2. filtrationThe resulting mixture was filtered
  3. customevaporated
  4. customThe residue was chromatographed (Isolera, 40 g silica cartridge, 0-100% ethyl acetate/petroleum benzine 40-60° C.)

出典と根拠

ORDレコード
ord-a0fa29c70bd24ac6b3f66ca2c6c68e3c
出典データセット
uspto-grants-2015_04
特許番号
US09012461B2

関連ノート

読み込み中…