Chlorosulfonic acid → HCID 135738542, compound

HRID 1532123Notes

Reaction equation

HRID 1532123 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:11][C:12](=[O:22])[C:13]2[CH:18]=[N:17][N:16]([CH2:19][CH2:20][CH3:21])[C:14]=2[N:15]=1)[CH3:2].[Cl:23][S:24](O)(=[O:26])=[O:25]>C(OCC)C>[Cl:23][S:24]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:10]2[NH:11][C:12](=[O:22])[C:13]3[CH:18]=[N:17][N:16]([CH2:19][CH2:20][CH3:21])[C:14]=3[N:15]=2)[CH:6]=1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 135738567HCID 135738567, compound

Product 1

HCID 135738542HCID 135738542, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-(2-Ethoxyphenyl)-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Example 1; 0.5 g, 0.0017 mol) was added portionwise to stirred chlorosulphonic acid (3 ml) at 0° C. and the resulting solution stirred at room temperature for 14 hours. The reaction mixture was then added dropwise to ice/water (20 g) and the aqueous solution thus obtained was extracted with dichloromethane (4×30 ml). The combined extracts were dried (Na2SO4) and the solvent evaporated under vacuum to give a white solid; trituration was diethyl ether (50 ml) gave the title compound (0.67 g, 100%), m.p. 177-180° C., which was used without further purification.

Workup

  1. customthe aqueous solution thus obtained
  2. extractionwas extracted with dichloromethane (4×30 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent evaporated under vacuum
  5. customto give a white solid

Sources & evidence

ORD record
ord-912cff114fe44be48cf1ec382402412a
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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