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Pyridine → Sodium 2-((1E,3Z,5E)-3-Bromo-5-(1,1-dimethyl-6,8-disulfonato-3-(3-sulfonatopropyl)-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dienyl)-1,1-dimethyl-3-(3-sulfonatopropyl)-1H-benzo[e]indolium-6,8-disulfonate

HRID 449534
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HRID 449534 반응식
[CH3:1][C:2]1([CH3:31])[C:10]2[C:9]3[CH:11]=[C:12]([S:19]([O-:22])(=[O:21])=[O:20])[CH:13]=[C:14]([S:15]([O-:18])(=[O:17])=[O:16])[C:8]=3[CH:7]=[CH:6][C:5]=2[N+:4]([CH2:23][CH2:24][CH2:25][S:26]([O-:29])(=[O:28])=[O:27])=[C:3]1[CH3:30].[Na+:32].[Na+].[Br-:34].Br/[C:36](=[CH:45]\[NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)/[CH:37]=[NH+]/C1C=CC=CC=1.N1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.C(O[C:63](=O)[CH3:64])(=O)C>C(OCC)C>[Br:34]/[C:55](=[CH:56]\[CH:57]=[C:58]1\[N:46]([CH2:45][CH2:36][CH2:37][S:19]([O-:22])(=[O:21])=[O:20])[C:47]2[CH:48]=[CH:49][C:50]3[C:64]([S:26]([O-:29])(=[O:28])=[O:27])=[CH:63][C:14]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:13][C:51]=3[C:52]=2[C:2]\1([CH3:3])[CH3:1])/[CH:54]=[CH:30]/[C:3]1[C:2]([CH3:31])([CH3:1])[C:10]2[C:9]3[CH:11]=[C:12]([S:19]([O-:22])(=[O:20])=[O:21])[CH:13]=[C:14]([S:15]([O-:18])(=[O:16])=[O:17])[C:8]=3[CH:7]=[CH:6][C:5]=2[N+:4]=1[CH2:23][CH2:24][CH2:25][S:26]([O-:29])(=[O:28])=[O:27].[Na+:32].[Na+:32].[Na+:32].[Na+:32].[Na+:32]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86649205Sodium 1,1,2-Trimethyl-3-(3-sulfonatopropyl)-1H-benzo[e]indolium-6,8-disulfonateHCID 178419561HCID 178419561, 화합물

생성물 1

HCID 86649203
Sodium 2-((1E,3Z,5E)-3-Bromo-5-(1,1-dimethyl-6,8-disulfonato-3-(3-sulfonatopropyl)-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dienyl)-1,1-dimethyl-3-(3-sulfonatopropyl)-1H-benzo[e]indolium-6,8-disulfonate
수율 50%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
115 °C

실험 절차

A 100 ml round bottom flask fitted with a reflux condenser was charged with sodium 1,1,2-trimethyl-3-(3-sulfonatopropyl)-1H-benzo[e]indolium-6,8-disulfonate (3) (565 mg, 1 mmol), (E)-N—((Z)-2-bromo-3-(phenylamino)allylidene)benzenaminium bromide (5) (150 mg, 0.5 mmol), and pyridine (1 ml). Acetic anhydride (10 ml) was added to the flask, and the mixture was heated at 115° C. for 2 h, cooled to room temperature, and diluted with 25 ml of ethyl ether. The resulting dark blue dye precipitate was collected by filtration, then dissolved in 20 ml of water and purified by preparative reverse-phase HPLC to afford the compound 6 as a blue powder (285 mg, 50%; UV/vis absorption max 674 nm).

후처리

  1. customA 100 ml round bottom flask fitted with a reflux condenser
  2. temperaturecooled to room temperature
  3. filtrationThe resulting dark blue dye precipitate was collected by filtration
  4. dissolutiondissolved in 20 ml of water
  5. custompurified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-28399a89bfa94eb69d49f288c02095d6
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481752B2

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