Carbamic acid, ethyl ester → HCID 178517451, compound

HRID 1076577Notes

Reaction equation

HRID 1076577 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14].[C:16](=O)([O:18]CC)[NH2:17]>CC(C)=O.[Cl-].[Zn+2].[Cl-]>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[NH:1][C:16](=[O:18])[N:17]=1

Participants

5

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 12202371HCID 12202371, compound

Product 1

HCID 178517451HCID 178517451, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 500 mg of 2-amino-3-(o-fluorobenzoyl)thiophene, 760 mg of ethyl carbamate and 46 mg of zinc chloride is heated at 200°C for 1 hour. After cooling, the reaction mixture is washed with chloroform and filtered to give crystals, which are disolved in acetone and filtered. The filtrate is condensed under reduced pressure to give 4-(o-fluorophenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 254° - 256°C. Recrystallization from acetone gives crystals having a melting point of 278° - 279°C (decomp.)

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture is washed with chloroform
  3. filtrationfiltered
  4. customto give crystals, which
  5. filtrationfiltered
  6. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-06a875fb2e8b4c568cf462308c54faa2
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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