Diethyl Ether → HCID 86738893, compound

HRID 851776Notes

Reaction equation

HRID 851776 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[Br-].[C:9]([CH2:12][CH2:13][N+:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=[CH:25][CH:26]=[CH:27]NC2C=CC=CC=2)=[CH:16][CH:15]=1)([OH:11])=[O:10].[CH3:35][CH:36]1[N:40]([CH2:41][CH2:42][CH2:43][S:44]([O-:47])(=[O:46])=[O:45])[C:39]2[C:48]3[C:53]([CH:54]=[CH:55][C:38]=2[S:37]1)=[CH:52][CH:51]=[CH:50][CH:49]=3.C(OCC)C>CS(C)=O.C(O)C>[C:9]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[CH:24][CH:25]=[CH:26][CH:27]=[CH:35][CH:36]2[N:40]([CH2:41][CH2:42][CH2:43][S:44]([O-:47])(=[O:45])=[O:46])[C:39]3[C:48]4[C:53]([CH:54]=[CH:55][C:38]=3[S:37]2)=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH:16]=[CH:15]1)([OH:11])=[O:10].[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 20501123HCID 20501123, compoundHCID 73681569HCID 73681569, compound

Product 1

HCID 86738893HCID 86738893, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

A solution of 3 ml of triethylamine in 100 ml of dimethylsulfoxide was added to 4 g of 1-(2-carboxyethyl)-4-(4-anilino-1,3-butadien-1-yl)-quinolinium bromide and 3 g of 3-(2-methylnaphtho[1,2-d]thiazolin-1-yl)-propane-1-sulfonate and the resulting mixture was subjected to reaction at 100° C. for 2 hours. After completion of the reaction, the reaction product was cooled, and diethyl ether was added, after which the resulting precipitate was collected by filtration to obtain a crude dye. It was boiled together with ethanol to obtain crystals, and the crystals were recrystallized from methanol containing a small quantity of triethylamine to obtain 0.9 g of the objective compound (melting point 219° C.) which was dark green. Its maximum absorption wavelength as measured in triethylamine-containing methanol was 760 nm.

Workup

  1. customthe resulting mixture was subjected to reaction at 100° C. for 2 hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction product was cooled
  4. filtrationafter which the resulting precipitate was collected by filtration
  5. customto obtain a crude dye
  6. customto obtain crystals
  7. customthe crystals were recrystallized from methanol containing a small quantity of triethylamine

Sources & evidence

ORD record
ord-02c9f105cb6342478dd485eac7d40e2f
Source dataset
uspto-grants-1983_05
Patent number
US04386146

Reaction notes

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