Carbamic acid, ethyl ester → HCID 21487724, compound

HRID 1076609Notes

Reaction equation

HRID 1076609 reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[C:6]([CH3:17])[C:7]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15].[C:18](=O)([O:20]CC)[NH2:19]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]2[S:4][CH:5]=[C:6]([CH3:17])[C:7]=2[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[N:19][C:18]1=[O:20]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 21537722HCID 21537722, compound

Product 1

HCID 21487724HCID 21487724, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 16.0 g of 2-methylamino-3-(o-chlorobenzoyl)-4-methylthiophene, 16.1 g of ethyl carbamate and 1.22 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-(o-chlorophenyl)-5-methyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 267.5° - 268.5°C (after recrystallization from chloroformethanol).

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-d9748854697741189bd1cac82b6eca8d
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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