Ethyl chloroformate → HCID 21838739, compound

HRID 1740498Notes

Reaction equation

HRID 1740498 reaction equation
[NH2:1][C:2]1[C:3]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1(C)C=CC=CC=1.ClCCl>[CH2:27]([O:26][C:24]([NH:1][C:2]1[C:3]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])=[O:25])[CH3:28]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformate2×HCID 11430Potassium CarbonateHCID 10705031HCID 10705031, compound

Product 1

HCID 21838739HCID 21838739, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 27.4 g (0.115 mol) of methyl 3-amino-6-methoxybenzo[b]thiophene-2-carboxylate, 38 g (0.275 mol) of potassium carbonate and 13.2 ml (0.138 mol) of ethyl chloroformate in 330 ml of toluene is heated at reflux for three hours. 7 ml (0.069 mol) of ethyl chloroformate are then added and the mixture is left heating at reflux for a further seven hours, with stirring. The mixture is then diluted with dichloromethane and washed with water. The organic phase is dried over sodium sulphate and the solvent is evaporated under reduced pressure. Recrystallization is carried out from a mixture of isopropanol and diisopropyl ether. 31.2 g of product are obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for three hours
  3. waitthe mixture is left
  4. temperatureheating
  5. temperatureat reflux for a further seven hours
  6. washwashed with water
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. customthe solvent is evaporated under reduced pressure
  9. customRecrystallization
  10. additionis carried out from a mixture of isopropanol and diisopropyl ether

Sources & evidence

ORD record
ord-12524a6cb5074c189b4559a6a97d5c7b
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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