Chlorosulfonic acid → 4-[5-Cyano-1-(3,4-dimethylphenyl)-4-(methylthio)-6-oxo-1,6-dihydropyrimidin-2-yl]benzenesulfonyl chloride

HRID 901935Notes

Reaction equation

HRID 901935 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:5][C:4]=1[S:24][CH3:25])#[N:2].[Cl:26][S:27](O)(=[O:29])=[O:28]>CO>[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[C:6]([C:18]2[CH:19]=[CH:20][C:21]([S:27]([Cl:26])(=[O:29])=[O:28])=[CH:22][CH:23]=2)=[N:5][C:4]=1[S:24][CH3:25])#[N:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 69220863HCID 69220863, compound

Product 1

HCID 865955254-[5-Cyano-1-(3,4-dimethylphenyl)-4-(methylthio)-6-oxo-1,6-dihydropyrimidin-2-yl]benzenesulfonyl chlorideYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-cyano-1-(3,4-dimethylphenyl)-4-(methylthio)-2-phenyl-6-oxo-1,6-dihydropyrimidine (3 g, 8.6 mmol) (obtained according to example 57) in chlorosulfonic acid (50.37 g, 432 mmol) was stirred at 0° C. for 2 hr and at ambient temperature for 24 hr and then poured onto ice and extracted with chloroform. The collected chloroform layer was dried over anhydrous Na2SO4 and concentrated in vacuo to yield crude compound, which was further purified by column chromatography using chloroform:methanol mixture as eluent to yield title compound (0.5 g, yield 13%). 1H-NMR (CDCl3):δ 2.37 (s, 3H), 2.65 (s, 3H), 2.68 (s, 3H), 7.26-7.55 (m, 7H). MS m/z:446.1 (M+).

Workup

  1. additionpoured onto ice
  2. extractionextracted with chloroform
  3. dry with materialThe collected chloroform layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto yield crude compound, which
  6. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-3d98eaebe3ea46e394a0ae451ba184d2
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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