1-Aminopyrene → HCID 21464477, compound

HRID 1940982Notes

Reaction equation

HRID 1940982 reaction equation
[NH2:1][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[Cl:18][S:19]([OH:22])(=O)=[O:20]>>[NH2:1][C:2]1[CH:3]=[C:4]([S:19]([Cl:18])(=[O:22])=[O:20])[C:5]2[CH:6]=[CH:7][C:8]3[C:17]4[C:16]=2[C:15]=1[CH:14]=[CH:13][C:12]=4[C:11]([S:19]([Cl:18])(=[O:22])=[O:20])=[CH:10][C:9]=3[S:19]([Cl:18])(=[O:22])=[O:20]

Participants

3

Reactant 2

HCID 153521-AminopyreneHCID 24638Chlorosulfonic acid

Product 1

HCID 21464477HCID 21464477, compoundYield 69%

Procedure

Dyes 2a, 2d and 3 were obtained from Eastman, and the following dyes were prepared as described previously: 2c (8); 2g (9). The syntheses of 2e, 2f, 2h, 2I and 2j were modeled after the sulfonation procedures described in (10). Thus, for 2f, a solution of finely powdered 1-aminopyrene (869 mg, 4 mmol) in 10 ml chlorosulfonic acid was stirred under argon atmosphere for 10 hours at room temperature. The solution was poured on 30 g of crushed ice and the crude product was collected by filtration, washed with 20 mL cold water and dried under argon to give 1.4 g of 8-amino-1,3,6-pyrenetrisulfonylchloride (69%). Hydrolysis of this chloride in basic water (NaOH, pH 8) gave a solution of 2f (8-amino-1,3,6-pyrenetrisulfonate). Analogous procedures were used to prepare 2g-2j, except replacing the 1-aminopyrene with the appropriate substituted pyrene starting material.

Workup

  1. customthe following dyes were prepared
  2. filtrationthe crude product was collected by filtration
  3. washwashed with 20 mL cold water
  4. customdried under argon

Sources & evidence

ORD record
ord-7367f15dc08445f39259ca6e046967e5
Source dataset
uspto-grants-1997_12
Patent number
US05701323

Reaction notes

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