p-Toluenesulfonic acid → HCID 10730123, compound

HRID 746375Notes

Reaction equation

HRID 746375 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[C:7]([CH2:16][C:17]([OH:19])=O)=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:5])=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[C:17](=[O:19])[CH2:16][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[S:3]1(=[O:5])=[O:4])[CH:13]=[CH:12][CH:11]=[CH:10]3

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57435923HCID 57435923, compound

Product 1

HCID 10730123HCID 10730123, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

This naphthalene-2-acetic acid (2.6 g, 9.4 mmol) was 12 hrs refluxed in 100 mL xylene with the addition of 0.2 g p-toluene-sulfonic acid. The reaction mixture was cooled, filtered, washed with water and concentrated. Recrystallization from ethanol gave 1.5 g (61%) 3,4-dihydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine 1,1-dioxide (melting point: 126-127° C.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washwashed with water
  4. concentrationconcentrated
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-3d9e95a4d9f94988949a1cb2542d96f7
Source dataset
uspto-grants-2008_07
Patent number
US07393843B2

Reaction notes

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