Chlorosulfonic acid → 4-[4-Chloro-6-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonyl chloride

HRID 1966332Notes

Reaction equation

HRID 1966332 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[N:10]=[C:9]([C:29]([F:32])([F:31])[F:30])[N:8]=1>>[Cl:6][C:7]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=2)[N:10]=[C:9]([C:29]([F:32])([F:30])[F:31])[N:8]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 100473384-Chloro-6-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 249626784-[4-Chloro-6-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonyl chlorideYield 65.59%

Conditions

Temperature
0 °C

Procedure

To a solution of chlorosulphonic acid (605 mmol, 40.4 ml) was added 4-chloro-6-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)pyrimidine (5.0 g, 12.1 mmol, prepared according to the procedure described in PCT/IB03/02879) slowly under continuous stirring at 0° C. until the completion of the addition. The reaction mixture was further stirred at 32° C. until TLC confirmed the completion. Subsequently the resulting reaction mass was poured slowly under vigorous stirring onto crushed ice and the solid obtained was filtered, washed thoroughly with water (100 ml) and extracted with ethyl acetate (3×200 ml). The combined organic layer was washed with brine (150 ml), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 4-{4-chloro-6-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)pyrimidin-5-yl}benzenesulfonyl chloride (2.75 g, yield 65.59%, purity by HPLC 98.17%); m.p: 207-210° C. 1H-NMR (400 MHz, CDCl3) δ: 3.01 (s, 3H), 7.511-7.515 (d, 2H), 7.53-7.67 (m, 1H), 7.72-7.76 (t, 1H), 7.86-7.89 (m, 3H), 8.11-8.13 (d, 1H). IR (KBr) cm−1: 1557, 1524; MS m/z: 511.6 (M+).

Workup

  1. customprepared
  2. stirringThe reaction mixture was further stirred at 32° C. until TLC
  3. customSubsequently the resulting reaction mass
  4. additionwas poured slowly
  5. stirringunder vigorous stirring
  6. customonto crushed ice
  7. customthe solid obtained
  8. filtrationwas filtered
  9. washwashed thoroughly with water (100 ml)
  10. extractionextracted with ethyl acetate (3×200 ml)
  11. washThe combined organic layer was washed with brine (150 ml)
  12. dry with materialdried over anhydrous sodium sulphate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3baec6c36dbc4f27a4bda08b0653ff58
Source dataset
uspto-grants-2013_04
Patent number
US08420653B2

Reaction notes

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