4-Hydrazinobenzenesulfonic acid → 2,3-Dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid

HRID 1667360

반응식

HRID 1667360 반응식
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)N.[CH3:13][CH:14]([C:23](=O)[CH3:24])[CH2:15][CH2:16][CH2:17][CH2:18][S:19]([OH:22])(=[O:21])=[O:20]>C(O)(=O)C>[CH3:24][C:23]1[C:14]([CH3:13])([CH2:15][CH2:16][CH2:17][CH2:18][S:19]([OH:22])(=[O:21])=[O:20])[C:8]2[C:3](=[CH:4][CH:5]=[C:6]([S:9]([OH:12])(=[O:11])=[O:10])[CH:7]=2)[N:1]=1

참가 물질

4

반응물 2

HCID 668254-Hydrazinobenzenesulfonic acidHCID 579033515-Methyl-6-oxoheptanesulfonic acid

생성물 1

HCID 593662262,3-Dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

4-Hydrazinobenzenesulfonic acid (1.88 g), 5-methyl-6-oxoheptanesulfonic acid (2.5 g) and acetic acid (50 ml) were mixed and heated under reflux for 6 hrs. The solvent was evaporated under vacuum, then the residue was triturated with 2-propanol to yield the crude product as a yellow solid. This was purified by HPLC as required (RPC18. Water+0.1% TFA). 1H-nmr (D2O) δ0.8-1.0 (2H, m), 1.55-1.65 (5H, =3H, s+2H, m), 2.16 (1H, ddd), 2.29 (1H, ddd), 2.75 (2H, m), 2.81 (partially d-exchanged methyl singlet), 7.71 (1H, d), 7.94 (1H, d) and 8.01 (1H, d). UV/Vis (Water+0.1% TFA): 269, 229 nm. MS (LCMS): MH+362. Acc. Mass: Found, 362.0729. MH+=C14H20NO6S2 requires 362.0732 (−0.8 ppm).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 6 hrs
  3. customThe solvent was evaporated under vacuum
  4. customthe residue was triturated with 2-propanol

출처 및 근거

ORD 기록
ord-c5d1693dd43f4a73ab4225e233761093
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044203B2

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