Carbamic acid, ethyl ester → HCID 12202409, compound

HRID 1076602Notes

Reaction equation

HRID 1076602 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([Cl:17])=[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:18](=O)([O:20]CC)[NH2:19]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]2[S:4][C:5]([Cl:17])=[CH:6][C:7]=2[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[N:19][C:18]1=[O:20]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 21537750HCID 21537750, compound

Product 1

HCID 12202409HCID 12202409, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 700 mg of 2-methylamino-3-(o-fluorobenzoyl)-5-chlorothiophene, 700 mg of ethyl carbamate and 50 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 under reduced pressure to give a residue, which is chromatographed on silica gel using chloroform as an eluent to give crystals of 1-methyl-4-(o-fluorophenyl)-6-chloro-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 192° - 194°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 under reduced pressure
  6. customto give a residue, which
  7. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-756a0ce8a4a34f8dab5a8218c5dd1156
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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