3-Nitrobenzenesulfonyl chloride → HCID 11797755, 화합물

HRID 324980

반응식

HRID 324980 반응식
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[N:7]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].CCN(C(C)C)C(C)C.[N+:29]([C:32]1[CH:33]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1)([O-:31])=[O:30]>C(Cl)Cl.[Cl-].[Na+].O>[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([S:38]([C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=3)(=[O:39])=[O:40])[CH:10]=[N:9][C:8]=2[N:7]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 3

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1014211,3-Dibutylxanthine

생성물 1

HCID 11797755HCID 11797755, 화합물수율 79%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
23 °C

실험 절차

To 404 mg (1.53 mmol) of 1,3-dibutyl-3,7-dihydro-purine-2,6-dione in 15 mL of CH2Cl2 at 23° C. was added 0.40 mL (296 mg, 2.29 mmol) i-Pr2NEt followed by 373 mg (1.68 mmol) of 3-nitrobenzenesulfonyl chloride. After stirring at 23° C. for 19 h, the reaction mixture was poured into 50 mL brine and extracted with 3×50 mL of EtOAc. The combined organics were successively washed with 1×50 mL sat. NaHCO3 solution, 1×50 mL H2O, 1×50 mL brine, dried over MgSO4, filtered and evaporated to an oily yellow solid. Flash chromatography on silica gel, eluting with CH2Cl2/EtOAc (40/1), gave a white solid. Recrystallization from hot hexanes/EtOAc gave 540 mg (1.20 mmol, a 79% yield) of the title compound as a white, crystalline solid. mp: 178-179° C.; 1H NMR (300 MHz, CDCl3); δ 0.88-0.98 (m, 6H), 1.22-1.42 (m, 4H), 1.50-1.61 (m, 2H), 1.63-1.75 (m, 2H), 3.92 (t, J=7.5 Hz, 2H), 4.07 (t, J=7.5 Hz, 2H) 7.86 (t, J=8.1 Hz, 1H), 8.34 (s, 1H), 8.55 (d, J=8.1 Hz, 1H), 8.77 (d, J=8.2 Hz, 1H), 9.01 (brt, 1H); IR (KBr, cm−1): 3142w, 2963m, 2935m, 2876w, 1716s, 1661s, 1538s, 1441m, 1396s, 1181s, 1130m, 761m, 670m; MS (ES) m/z (relative intensity): 450 (M++H, 100).

후처리

  1. extractionextracted with 3×50 mL of EtOAc
  2. washThe combined organics were successively washed with 1×50 mL sat. NaHCO3 solution, 1×50 mL H2O, 1×50 mL brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to an oily yellow solid
  6. washFlash chromatography on silica gel, eluting with CH2Cl2/EtOAc (40/1)
  7. customgave a white solid
  8. customRecrystallization from hot hexanes/EtOAc
  9. customgave 540 mg (1.20 mmol

출처 및 근거

ORD 기록
ord-a2970b702dea4bb8afa72f1548267d7d
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06221874B1

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