Chlorosulfonic acid → HCID 22908976, compound

HRID 1378991Notes

Reaction equation

HRID 1378991 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]([CH2:16][CH2:17][CH3:18])[C:5]=2[N:4]=[C:3]1/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl[S:28]([OH:31])(=[O:30])=[O:29]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]([CH2:16][CH2:17][CH3:18])[C:5]=2[N:4]=[C:3]1/[CH:19]=[CH:20]/[C:21]1[CH:22]=[CH:23][C:24]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 6448583141807-86-5

Product 1

HCID 22908976HCID 22908976, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(E)-7-Methyl-1,3-dipropyl-8-styrylxanthine (WO92/06976) (500 mg, 1.42 mmol) was dissolved in chloroform (5 ml), and chlorosulfonic acid (0.28 ml, 4.26 mmol) was added dropwise thereto at 0° C. The resulting solution was heated under reflux for 3 hours and then poured into 20 ml of ice-water. The chloroform layer was separated and the aqueous layer was extracted 5 times with tetrahydrofuran. The combined organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 240 mg (yield 39%) of Compound 31 as a pale yellow powder.

Workup

  1. customat 0° C
  2. temperatureThe resulting solution was heated
  3. temperatureunder reflux for 3 hours
  4. customThe chloroform layer was separated
  5. extractionthe aqueous layer was extracted 5 times with tetrahydrofuran
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2db91da788d14521885e62a37252e57e
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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