Pyridine → HCID 86649203, compound

HRID 449534Notes

Reaction equation

HRID 449534 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 86649203HCID 86649203, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
115 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-28399a89bfa94eb69d49f288c02095d6
Source dataset
uspto-grants-2013_07
Patent number
US08481752B2

Reaction notes

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