Chlorosulfonic acid → 4-Chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzenesulfonyl chloride

HRID 1891382Notes

Reaction equation

HRID 1891382 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[C:15]([C:16]#[N:17])=[CH:14][C:13]([C:18]([F:21])([F:20])[F:19])=[N:12][CH:11]=1.[Cl:22][S:23](O)(=[O:25])=[O:24]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([C:10]2[CH:11]=[N:12][C:13]([C:18]([F:21])([F:19])[F:20])=[CH:14][C:15]=2[C:16]#[N:17])=[CH:4][C:5]([S:23]([Cl:22])(=[O:25])=[O:24])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 684720965-(2-Chloro-4-methoxy-phenyl)-2-trifluoromethylisonicotinonitrile

Product 1

HCID 866435054-Chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 5-(2-chloro-4-methoxy-phenyl)-2-trifluoromethylisonicotinonitrile (0.7 g, 2.24 mmol) in chloroform (6 mL), was added to ClSO3H (0.62 mL). The solution was stirred at rt for 16 hrs. The solvent was removed and MeCN (3 mL) was added, followed by addition of POCl3 (3 mL). The mixture was heated at 60° C. for 16 hrs, then concentrated. The remainder was poured into ice water with stirring. The resulting solid was filtered, dried in vacuo over 2 days to yield 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzenesulfonyl chloride (0.79 g) as a pale yellow solid. tR=2.92 min (method 1).

Workup

  1. customThe solvent was removed
  2. additionMeCN (3 mL) was added
  3. additionfollowed by addition of POCl3 (3 mL)
  4. temperatureThe mixture was heated at 60° C. for 16 hrs
  5. concentrationconcentrated
  6. additionThe remainder was poured into ice water
  7. stirringwith stirring
  8. filtrationThe resulting solid was filtered
  9. customdried in vacuo over 2 days

Sources & evidence

ORD record
ord-6cc08bc96af24daaac77dbe9cf38596d
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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