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

HRID 1473103

반응식

HRID 1473103 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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.)

출처 및 근거

ORD 기록
ord-a0fa29c70bd24ac6b3f66ca2c6c68e3c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012461B2

연결된 노트

불러오는 중…