Carbamic acid, ethyl ester → HCID 178437796, compound

HRID 1076614Notes

Reaction equation

HRID 1076614 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7](=O)[CH2:8][CH3:9].[C:11](=O)([O:13]CC)[NH2:12]>[Cl-].[Zn+2].[Cl-].O>[CH2:8]([C:7]1[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[NH:1][C:11](=[O:13])[N:12]=1)[CH3:9]

Participants

5

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 12202375HCID 12202375, compound

Product 1

HCID 178437796HCID 178437796, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4.0 g of 2-amino-3-propionylthiophene, 8.9 g of ethyl carbamate and 0.53 g of zinc chloride is heated at 200°C for 1 hour. After cooling, the resulting material is treated with hot water and then filtered. The filtrate is extracted with chloroform and the insoluble matter is washed with hot chloroform. The chloroform extracts were combined and washed with water. After removing the chloroform by distillation under reduced pressure, the resulting residue is crystallized from ethanol to give 4-ethyl-1,2-dihydrothieno[2,3-d]pyrimidine-2-one. Recrystallized from a mixture of ethanol and chloroform, there are obtained crystals having a melting point of 217° - 220°C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. extractionThe filtrate is extracted with chloroform
  4. washthe insoluble matter is washed with hot chloroform
  5. washwashed with water
  6. customAfter removing the chloroform
  7. distillationby distillation under reduced pressure
  8. customthe resulting residue is crystallized from ethanol

Sources & evidence

ORD record
ord-067d728cbae747fb92540ceef6e64197
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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