p-Toluenesulfonic acid → HCID 18350498, compound

HRID 430426Notes

Reaction equation

HRID 430426 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:19][C:3]=1[C:4]([CH:6]([C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])C(OC(C)(C)C)=O)=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:22]=[C:21]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=[CH:19][C:3]=1[C:4](=[O:5])[CH2:6][C:14]([CH:16]1[CH2:17][CH2:18]1)=[O:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18350471HCID 18350471, compound

Product 1

HCID 18350498HCID 18350498, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

t-Butyl 2-[2-chloro-4-(methylsulphonylamino)benzoyl]-3-cyclopropyl-3-oxopropionate (2 g) was dissolved in toluene and p-toluenesulphonic acid (0.2 g) was added. The mixture was stirred and heated at reflux for 0.5 hours. It was cooled, washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 1-[2-chloro-4-(methylsulphonylamino)phenyl]-3-cyclopropylpropan-1,3-dione (1.48 g) as a white solid, m.p. 119.9-121.6° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.5 hours
  3. temperatureIt was cooled
  4. washwashed with water
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c6f4b4e9122f444da17ce69a39a31fff
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

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