Acetic Anhydride → HCID 86699468, compound

HRID 1425466Notes

Reaction equation

HRID 1425466 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:17]([CH3:19])([CH3:18])[C:16]([CH3:20])=[N:15][C:5]2=[N+:6]([CH2:8][CH2:9][CH2:10][S:11]([O-:14])(=[O:13])=[O:12])[CH:7]=1.[CH3:21][C:22]1[C:30]([CH3:32])([CH3:31])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([S:33]([O-:36])(=[O:35])=[O:34])[CH:28]=2)[N+:23]=1[CH2:37][CH2:38][CH2:39][S:40]([O-:43])(=[O:42])=[O:41].[Na+:44].[Br-].[Br:46]/[C:47](=[CH:56]\NC1C=CC=CC=1)/[CH:48]=[NH+]/C1C=CC=CC=1.C(OC(=O)C)(=O)C>C(OCC)C.N1C=CC=CC=1>[Br:46]/[C:47](/[CH:56]=[CH:20]/[C:16]1[C:17]([CH3:19])([CH3:18])[C:4]2[C:5]([N:15]=1)=[N+:6]([CH2:8][CH2:9][CH2:10][S:11]([O-:14])(=[O:13])=[O:12])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:48]\[CH:21]=[C:22]1\[N:23]([CH2:37][CH2:38][CH2:39][S:40]([O-:43])(=[O:42])=[O:41])[C:24]2[C:29]([C:30]\1([CH3:31])[CH3:32])=[CH:28][C:27]([S:33]([O-:36])(=[O:35])=[O:34])=[CH:26][CH:25]=2.[Na+:44].[Na+:44]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 71692790HCID 71692790, compoundHCID 866994663-(5-Chloro-2,3,3-trimethyl-3H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)propane-1-sulfonateHCID 178419561HCID 178419561, compound

Product 1

HCID 86699468HCID 86699468, compoundYield 130.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
115 °C

Procedure

A 100-mL round-bottom flask fitted with a reflux condenser was charged with 3-(5-chloro-2,3,3-trimethyl-3H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)propane-1-sulfonate (55, 500 mg), sodium 2,3,3-trimethyl-1-(3-sulfonatopropyl)-3H-indolium-5-sulfonate (4, 500 mg), (E)-N—((Z)-2-bromo-3-(phenylamino)allylidene)benzenaminium bromide (8, 100 mg), pyridine (1 mL), and acetic anhydride (10 mL) were added to the flask. The mixture was heated at 115° C. for 2 h, allowed to cool to room temperature, and diluted with ethyl ether (25 mL). The resulting dark blue dye precipitate was collected by filtration, dissolved in water (20 mL), and purified by preparative reverse-phase HPLC to afford the 9 as a blue powder (285 mg, 50%, UV 668 nm).

Workup

  1. customA 100-mL round-bottom flask fitted with a reflux condenser
  2. additionwere added to the flask
  3. temperatureto cool to room temperature
  4. filtrationThe resulting dark blue dye precipitate was collected by filtration
  5. dissolutiondissolved in water (20 mL)
  6. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-3df61d7f99b84271843b342e59def39f
Source dataset
uspto-grants-2015_01
Patent number
US08927719B2

Reaction notes

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