Dansyl chloride → N-Dansyl-3,5-di-(3-methylmaleimido)aniline

HRID 76769

반응식

HRID 76769 반응식
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].FC(F)(F)C([O-])=O.[CH3:25][C:26]1[C:31](=[O:32])[N:30]([C:33]2[CH:34]=[C:35]([CH:37]=[C:38]([N:40]3[C:44](=[O:45])[C:43]([CH3:46])=[CH:42][C:41]3=[O:47])[CH:39]=2)[NH3+:36])[C:28](=[O:29])[CH:27]=1>N1C=CC=CC=1>[S:1]([NH:36][C:35]1[CH:37]=[C:38]([N:40]2[C:44](=[O:45])[C:43]([CH3:46])=[CH:42][C:41]2=[O:47])[CH:39]=[C:33]([N:30]2[C:31](=[O:32])[C:26]([CH3:25])=[CH:27][C:28]2=[O:29])[CH:34]=1)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2]

참가 물질

4

반응물 2

HCID 11801Dansyl chlorideHCID 68007149HCID 68007149, 화합물

생성물 1

HCID 50918100N-Dansyl-3,5-di-(3-methylmaleimido)aniline수율 16%

시약·촉매·용매 1

HCID 1049Pyridine용매2회

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온도
25 °C

실험 절차

Dansyl chloride (139 mg, 0.517 mmol) in pyridine (3 mL) was added to a pyridine solution of 4 (200 mg, 0.517 mmol). The resulting mixture was stirred at 25° C. for 18 hours after which the volatiles were evaporated under reduced pressure. The resulting oil was taken back in CHCl3 and the organic phase was washed with aqueous saturated Na2CO3, dried over MgSO4 and evaporated. The crude was purified by flash chromatography on silica gel (Tol/EtOAc 10%) giving 5 as a light green solid (40 mg, 0.074 mmol, 16%). 1H NMR (400 MHz, (CD3)2CO) δ 9.71 (s, 1H), 8.56 (d, J=8.4 Hz, 1H), 8.51 (d, J=8.8 Hz, 1H), 8.39 (dd, J1=1.2, 7.2 Hz, 1H), 7.62-7.58 (td, J=1.2, 7.2 Hz, 2H), 7.28-7.27 (m, 3H), 7.11 (t, J=2.0 Hz, 1H), 6.63-6.61 (m, 2H); 13C NMR (75 MHz, (CD3)2CO) δ 171.3, 170.4, 152.8, 135.4, 134.0, 131.7, 131.5, 130.3, 130.2, 129.6, 128.7, 124.9, 119.8, 119.6, 116.6, 115.9, 46.3, 12.1; HRMS (ESI) Calculated for C28H25N4O6S [M+H]+: 545.1516. Found: 545.1489. m.p.: 230° C.

후처리

  1. customwere evaporated under reduced pressure
  2. washthe organic phase was washed with aqueous saturated Na2CO3
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel (Tol/EtOAc 10%)

출처 및 근거

ORD 기록
ord-dd771b82ecab4068b86c1072bfaa75c4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835641B2

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