Methyl Carbamate → HCID 19352271, compound

HRID 726887Notes

Reaction equation

HRID 726887 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].[C:18](=[O:22])([O:20][CH3:21])[NH2:19]>C1(C)C=CC=CC=1>[CH3:21][O:20][C:18]([NH:19][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:22]

Participants

4

Reactant 2

HCID 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-totuenesulfonic 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-efa5f0a4fd88486c88d143f1ed4449d7
Source dataset
uspto-grants-1998_01
Patent number
US05710336

Reaction notes

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