Dabsyl chloride → 4-(4-Dimethylamino-phenylazo)-n-(3-oxo-2,3-dihydro-7-oxa-1,2-diaza-benzo[de]anthracen-10-ylmethyl)-benzenesulfonamide

HRID 915795

반응식

HRID 915795 반응식
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.[CH3:21][N:22]([C:24]1[CH:29]=[CH:28][C:27]([N:30]=[N:31][C:32]2[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)[CH3:23]>CN(C=O)C>[CH3:21][N:22]([CH3:23])[C:24]1[CH:25]=[CH:26][C:27]([N:30]=[N:31][C:32]2[CH:37]=[CH:36][C:35]([S:38]([NH:1][CH2:2][C:3]3[CH:16]=[CH:15][C:14]4[O:13][C:12]5[C:7]6=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]6[C:5]=4[CH:4]=3)[CH:9]=[CH:10][CH:11]=5)(=[O:40])=[O:39])=[CH:34][CH:33]=2)=[CH:28][CH:29]=1

참가 물질

4

반응물 2

HCID 91660Dabsyl chlorideHCID 1119635510-(Aminomethyl)[1]benzopyrano[4,3,2-de]phthalazin-3(2H)-one

생성물 1

HCID 112382184-(4-Dimethylamino-phenylazo)-n-(3-oxo-2,3-dihydro-7-oxa-1,2-diaza-benzo[de]anthracen-10-ylmethyl)-benzenesulfonamide수율 59%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 49(0.5 mmol) in anhydrous DMF (20 mL) was added 4-dimethylaminoazobenzene-4′-sulfonyl chloride (0.5 mmol). The mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated in vacuo, and 50 mL of 50% EtOAc in hexanes was added. The precipitate was formed and collected through filtration. The crude product was recrystallized in 50% ethanol to afford a orange solid 55 in 59% yield. MS (ES+): 553; Mp:>300° C.; 1H-NMR (DMSO-d6, 400 MHz): 12.63 (s, 1H), 7.90 (d, J=2.0 Hz, 1H), 7.86-7.74 (m, 6H), 7.67 (d, J=9.0 Hz, 2H), 7.62 (dd, J=6.6 and 2.5 Hz, 1H), 7.44 (dd, J=8.5 and 2.0 Hz, 1H), 7.30 (d, J=8.5 Hz, 1H), 6.81 (d, J=9.0 Hz, 2H), 4.15 (s, 2H), 3.09 (s, 6H); Anal. Calcd. for C29H24N6O4S.(1.3H2O): C, 60.47; H, 4.65; N, 14.59; S, 5.57. Found: C, 60.72; H, 4.93; N, 15.39; S, 4.93.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo, and 50 mL of 50% EtOAc in hexanes
  2. additionwas added
  3. customThe precipitate was formed
  4. filtrationcollected through filtration
  5. customThe crude product was recrystallized in 50% ethanol

출처 및 근거

ORD 기록
ord-d4389d397a24477ea3ec938f19864c7c
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268138B2

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