Carbamic acid, ethyl ester → HCID 21487718, compound

HRID 1076588Notes

Reaction equation

HRID 1076588 reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[C:6]([CH3:16])[C:7]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17](=O)([O:19]CC)[NH2:18]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]2[S:4][CH:5]=[C:6]([CH3:16])[C:7]=2[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:18][C:17]1=[O:19]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 21537710HCID 21537710, compound

Product 1

HCID 21487718HCID 21487718, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 2.0 g of 2-methylamino-3-benzoyl-4-methylthiophene, 2.3 g of ethyl carbamate and 0.18 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 recrystallized from chloroform-ethanol to give 1-methyl-4-phenyl-5-methyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 275° - 280°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 chloroform-ethanol

Sources & evidence

ORD record
ord-6736735500324c9e85813ccb143fd980
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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