Sodium Chloride → HCID 43652982, compound

HRID 1444605Notes

Reaction equation

HRID 1444605 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][S:12]([C:15]3[CH:19]=[C:18]([Cl:20])[S:17][C:16]=3[Cl:21])(=[O:14])=[O:13])[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[Na+].[Na+].[Cl-].C(Cl)Cl>CC(C)=O.O>[O:4]=[C:5]1[CH2:6][CH2:7][CH:8]([NH:11][S:12]([C:15]2[CH:19]=[C:18]([Cl:20])[S:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 686794592,5-Dichloro-N-1,4-dioxaspiro[4.5]dec-8-yl-3-thiophenesulfonamide

Product 1

HCID 43652982HCID 43652982, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

p-TosOH×H2O 4 g (21.0 mmol) was added to a solution of 2,5-dichloro-thiophene-3-sulfonic acid-(1,4-dioxa-spiro[4.5]dec-8-yl)-amide 894 mg (2.40 mmol) in acetone (10 ml) and water (1 ml) and stirring was performed for 6 h at RT. After addition of aqueous 1M NaOH (100 ml) and aqueous saturated NaCl solution (100 ml), extraction was performed with CH2Cl2 (3×200 ml). After separation of the organic phases, drying over Na2SO4 and filtration, the solvent was removed by distillation. After purification by means of column chromatography, the product 2,5-dichloro-thiophene-3-sulfonic acid (4-oxo-cyclohexyl)-amide 634 mg (80% of theoretical) was obtained.

Workup

  1. customAfter separation of the organic phases
  2. dry with materialdrying over Na2SO4 and filtration
  3. customthe solvent was removed by distillation
  4. customAfter purification by means of column chromatography

Sources & evidence

ORD record
ord-83f75e5d018a49699f80180ab0ef3f04
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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