Pyridine → HCID 178427731, compound

HRID 20619Notes

Reaction equation

HRID 20619 reaction equation
[Na+:1].[Na+].[CH3:3][C:4]1([CH2:35][CH2:36][CH2:37][S:38]([OH:41])(=[O:40])=[O:39])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13]([OH:16])(=[O:15])=[O:14])[CH:11]=2)[N+:6]([CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:22])=[O:21])=[C:5]1/[CH:24]=[CH:25]/[CH:26]=[CH:27]/NC1C=CC=CC=1.[Na].[C:43]([CH2:46][CH2:47][CH2:48][C:49]1([CH3:70])[C:57]2[C:52](=[CH:53][CH:54]=[C:55]([S:58]([O-:61])(=[O:60])=[O:59])[CH:56]=2)[N+:51]([CH2:62][CH2:63][CH2:64][S:65]([OH:68])(=[O:67])=[O:66])=[C:50]1[CH3:69])([OH:45])=[O:44].N1C=CC=CC=1.CCOCC>C(O)(=O)C.C(OC(=O)C)(=O)C>[Na+:1].[Na+:1].[Na+:1].[Na+:1].[C:43]([CH2:46][CH2:47][CH2:48][C:49]1([CH3:70])[C:57]2[C:52](=[CH:53][CH:54]=[C:55]([S:58]([OH:61])(=[O:60])=[O:59])[CH:56]=2)[N:51]([CH2:62][CH2:63][CH2:64][S:65]([OH:68])(=[O:66])=[O:67])/[C:50]/1=[CH:69]/[CH:27]=[CH:26]/[CH:25]=[CH:24]/[C:5]1[C:4]([CH3:3])([CH2:35][CH2:36][CH2:37][S:38]([OH:41])(=[O:39])=[O:40])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13]([OH:16])(=[O:15])=[O:14])[CH:11]=2)[N+:6]=1[CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:21])=[O:22])([OH:45])=[O:44]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 874978823-(3-carboxypropyl)-2,3-dimethyl-5-sulfonato-1-(3-sulfopropyl)-3H-indolium sodium saltHCID 1317282033-methyl-2-((1E,3E)-4-phenylamino-buta-1,3-dienyl)-5-sulfo-1,3-bis-(3-sulfo-propyl)-3H-indolium disodium salt

Product 1

HCID 178427731HCID 178427731, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

642 mg (1 mmol) 3-methyl-2-((1E,3E)-4-phenylamino-buta-1,3-dienyl)-5-sulfo-1,3-bis-(3-sulfo-propyl)-3H-indolium disodium salt and 483 mg (1 mmol) 3-(3-Carboxypropyl)-2,3-dimethyl-5-sulfonato-1-(3-sulfopropyl)-3H-indolium sodium salt were dissolved in a mixture of 10 ml acetic acid and 10 ml acetic anhydride. Five ml pyridine was added. The solution was stirred under reflux for 15 min. Twenty ml ether was added after cooling to room temperature. The obtained precipitate (mixture of the diastereomers OB-5.5a and OB-5.5b) was extracted by suction, washed with ether, and dried.

Workup

  1. temperatureunder reflux for 15 min
  2. additionThe obtained precipitate (mixture of the diastereomers
  3. extractionand OB-5.5b) was extracted by suction
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-c883adedf8324d22b12958b209992724
Source dataset
uspto-grants-2010_06
Patent number
US07745640B2

Reaction notes

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