p-Toluenesulfonic acid → HCID 19352271, compound

HRID 1636642Notes

Reaction equation

HRID 1636642 reaction equation
O=[C:2]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[O:16][CH3:17])[C:3]([OH:5])=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:29](=[O:33])([O:31][CH3:32])[NH2:30]>C1(C)C=CC=CC=1>[CH3:32][O:31][C:29]([NH:30][C:2]1[C:3](=[O:5])[O:4][CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=2[O:16][CH3:17])[CH:6]=1)=[O:33]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11722Methyl CarbamateHCID 54562540HCID 54562540, compound

Product 1

HCID 19352271HCID 19352271, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

300 g of 2-keto-4-(2,3-dimethoxyphenyl)-3-butenoic acid, 2680 ml of toluene, 13.4 g of p-toluenesulfonic acid and 133.8 g of methyl carbamate are placed into a 6 l 4-necked round-bottomed flask in an oil-bath, the mixture is heated to 105° C. for 4 hours with stirring, and the present water is removed azeotropically, the mixture is filtered and the solution is evaporated to dryness under vacuum, then the residue is triturated for about 2 hours with 1260 ml of Et2O, filtered washing with petroleum ether (40-70° C.) and dried under vacuum at 60° C. 313.00 g are obtained. (Yield 94%).

Workup

  1. customthe present water is removed azeotropically
  2. filtrationthe mixture is filtered
  3. customthe solution is evaporated to dryness under vacuum
  4. customthe residue is triturated for about 2 hours with 1260 ml of Et2O
  5. filtrationfiltered
  6. washwashing with petroleum ether (40-70° C.)
  7. customdried under vacuum at 60° C
  8. custom313.00 g are obtained

Sources & evidence

ORD record
ord-b4ac56904a3f4635a0f67711297ed7d6
Source dataset
uspto-grants-2000_03
Patent number
US06034277

Reaction notes

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