Carbamic acid, ethyl ester → HCID 12202407, compound

HRID 1076597Notes

Reaction equation

HRID 1076597 reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8](=O)[CH2:9][CH3:10].[C:12](=O)([O:14]CC)[NH2:13]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]2[S:4][CH:5]=[CH:6][C:7]=2[C:8]([CH2:9][CH3:10])=[N:13][C:12]1=[O:14]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 12202406HCID 12202406, compound

Product 1

HCID 12202407HCID 12202407, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 0.59 g of 2-methylamino-3-propionylthiophene, 1.18 g of ethyl carbamate and 0.07 g of zinc chloride is heated at 200°C for 1 hour. After cooling, the reaction mixture is extracted with chloroform. The extracts are combined, washed with water, dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue is chromatographed on silica gel using chloroform as an eluent to give 1-methyl-4-ethyl-1,2-dihydrothieno[ 2,3-d]pyrimidin-2-one as crystals having a melting point of 155.5°-156.5°C (after recrystallization from ethanol).

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture is extracted with chloroform
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-5f681cfe0eae4a64a81bad97c832b164
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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