Chlorosulfonic acid → HCID 86625113, compound

HRID 1952299Notes

Reaction equation

HRID 1952299 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[N:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=4)[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>>[NH2:28][C:25]1[C:24]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:23][C:22]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3[C:9]2[CH:10]=[CH:11][N:6]=[CH:7][CH:8]=2)=[CH:27][N:26]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 66781630HCID 66781630, compound

Product 1

HCID 86625113HCID 86625113, compoundYield 47%

Procedure

To cold (0° C.) chlorosulfonic acid (15 mL) under vigorous stirring was added 5-[4-(4-pyridinyl)-6-quinolinyl]-2-pyridinamine (4.348 g, 14.57 mmol) portionwise. The reaction mixture was then heated at reflux for 16 hrs. Upon cooling to room temperature, LCMS indicated 47% of the title compound MS(ES)+m/e 396.9 [M+]+ and 37% of sulfonic acid by-product MS(ES)+ m/e 379.1 [M+]+. A 2 mL aliquot of this 0.456M solution of the title compound was used in the next reaction without further workup.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 16 hrs

Sources & evidence

ORD record
ord-f1599db315844f75b69dfb436e40b514
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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