p-Toluenesulfonic acid → HCID 18350498, compound

HRID 2393002Notes

Reaction equation

HRID 2393002 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 (MgSO4) 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 (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-436a0c49f5324dc0a9a57c0c39f15da7
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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