Benzothiazolium, 3-(2-carboxyethyl)-2-methyl-, bromide (1:1) → 2-[(3-Iminoisoindol-1-yl)methylene]-3-carboxyethyl benzothiazolium bromide

HRID 462509Notes

Reaction equation

HRID 462509 reaction equation
N=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[NH:11])[NH:3]1.[Br-:12].[CH3:13][C:14]1[S:15][C:16]2[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=2[N+:18]=1[CH2:19][CH2:20][C:21]([OH:23])=[O:22]>O>[Br-:12].[NH:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH:13]=[C:14]2[NH+:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:17]3[CH:24]=[CH:25][CH:26]=[CH:27][C:16]=3[S:15]2)=[N:3]1

Participants

4

Reactant 2

HCID 108766Benzothiazolium, 3-(2-carboxyethyl)-2-methyl-, bromide (1:1)HCID 178508669HCID 178508669, compound2×

Product 1

HCID 867400882-[(3-Iminoisoindol-1-yl)methylene]-3-carboxyethyl benzothiazolium bromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Three grams (0.02 mole) of 1,3-diiminoisoindoline was dissolved in 25 ml of warm water. Three grams (0.01 mole) of 2-methyl-3-carboxyethyl benzothiazolium bromide was added to the solution. A molar excess of 1,3-diiminoisoindoline was employed to avoid bis substitution. The solution was stirred and heated on a steam bath for 10 minutes. An orange solid separated from the solution. The solution was then cooled and the solid collected by filtration. The dye was redissolved in hot water with the aid of sodium hydroxide. The solution was filtered, and the filtrate was acidified with excess acetic acid to reprecipitate the dye. The dye was washed with water and methanol and vacuum dried at 70° C.

Workup

  1. temperatureheated on a steam bath for 10 minutes
  2. customAn orange solid separated from the solution
  3. temperatureThe solution was then cooled
  4. filtrationthe solid collected by filtration
  5. dissolutionThe dye was redissolved in hot water with the aid of sodium hydroxide
  6. filtrationThe solution was filtered
  7. washThe dye was washed with water and methanol and vacuum
  8. customdried at 70° C.

Sources & evidence

ORD record
ord-f2668e6da42a42bf9ae7bc67c3ff6a69
Source dataset
uspto-grants-1985_05
Patent number
US04515955

Reaction notes

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