Chlorosulfonic acid → HCID 86630361, compound

HRID 1674516Notes

Reaction equation

HRID 1674516 reaction equation
[O:1]([C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][S:20](O)(=[O:22])=[O:21]>>[Cl:19][S:20]([C:5]1[CH:4]=[CH:3][C:2]([O:1][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:9]=2)=[CH:7][CH:6]=1)(=[O:22])=[O:21]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 46114364HCID 46114364, compound

Product 1

HCID 86630361HCID 86630361, compound

Procedure

To chlorosulfonic acid (20 mL) was dropped ethyl 6-phenoxynicotinate (5.6 g) on ice bath, and the reaction mixture was stirred for 15 minutes at room temperature, and 3 hours at 60° C. To reaction mixture was added ice, and extracted with tert-butyl methyl ether. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound (7.5 g) having the following physical data.

Workup

  1. custom3 hours
  2. customat 60° C
  3. customTo reaction mixture
  4. additionwas added ice
  5. extractionextracted with tert-butyl methyl ether
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-388eddbc6b7c481480e7debfc8d7d5c7
Source dataset
uspto-grants-2011_08
Patent number
US08003642B2

Reaction notes

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