Carbamic acid, ethyl ester → HCID 12202395, compound

HRID 1076605Notes

Reaction equation

HRID 1076605 reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15].[C:17](=O)([O:19]CC)[NH2:18]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]2[S:4][CH:5]=[CH:6][C:7]=2[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[N:18][C:17]1=[O:19]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 21537760HCID 21537760, compound

Product 1

HCID 12202395HCID 12202395, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 500 mg of 2-methylamino-3-(o-fluorobenzoyl)thiophene, 716 mg of ethyl carbamate and 44 mg 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 and, the residue is recrystallized from ethanol to give 1-methyl-4-(o-fluorophenyl)-1,2-dihyrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 221.5° - 222°C.

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 recrystallized from ethanol

Sources & evidence

ORD record
ord-8336edffc21445b1b3455cae7c1ea2f1
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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