Carbamic acid, ethyl ester → HCID 178421810, compound

HRID 1076572Notes

Reaction equation

HRID 1076572 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:16])=[CH:5][C:6]=1[C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14].[C:17](=O)([O:19]CC)[NH2:18]>[Cl-].[Zn+2].[Cl-]>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[C:6]2[CH:5]=[C:4]([CH3:16])[S:3][C:2]=2[NH:1][C:17](=[O:19])[N:18]=1

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 21537719HCID 21537719, compound

Product 1

HCID 178421810HCID 178421810, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 17.85 g of 2-amino-3-(o-fluorobenzoyl)-5-methylthiophene, 25.69 g of ethyl carbamate and 1.55 g of zinc chloride is heated at 200°C for 30 minutes. After cooling, the reaction mixture is washed with chloroform, then with water, and filtered to give 4-(o-fluorophenyl)-6-methyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystalline solids. Recrystallization from chloroform-ethanol gives crystals having a melting point of 282° - 284°C.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture is washed with chloroform
  3. filtrationwith water, and filtered

Sources & evidence

ORD record
ord-2da99ece03dc4f7bbb6a2b3b3c8c9d3f
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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