Carbamic acid, ethyl ester → HCID 21537732, compound

HRID 1076599Notes

Reaction equation

HRID 1076599 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([CH2:17][CH3:18])=[CH:6][C:7]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15].[C:19](=O)([O:21]CC)[NH2:20]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]2[S:4][C:5]([CH2:17][CH3:18])=[CH:6][C:7]=2[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[N:20][C:19]1=[O:21]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 13229177HCID 13229177, compound

Product 1

HCID 21537732HCID 21537732, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 11.7 g of 2-methylamino-3-(o-chlorobenzoyl)-5-ethylthiophene, 11.18 g of ethyl carbamate and 0.86 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 contentrated to dryness under reduced pressure. The residue is chromatographed on silica gel using chloroform as an eluent to give 1-methyl-4-(o-chlorophenyl)-6-ethyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 99°-χ°C (after recrystallization from isopropanol).

Workup

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

Sources & evidence

ORD record
ord-4d68e10762a94ab99df62454240685ba
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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