Carbamic acid, ethyl ester → HCID 21537717, compound

HRID 1076593Notes

Reaction equation

HRID 1076593 reaction equation
[CH3:1][NH:2][C:3]1[S:7][C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[C:4]=1[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20](=O)([O:22]CC)[NH2:21]>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:3]2[S:7][C:6]3[CH2:8][CH2:9][CH2:10][CH2:11][C:5]=3[C:4]=2[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:21][C:20]1=[O:22]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 16486755HCID 16486755, compound

Product 1

HCID 21537717HCID 21537717, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 1.5 g of 2-methylamino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene, 1.5 g of ethyl carbamate and 0.11 g of zinc chloride is heated at 200°C for 1 hour. After cooling, the reaction mixture is extracted with chloroform. The chloroform extracts are combined, washed with water, dried over sodium sulfate and concentrated to dryness under reduced pressure and residue is recrystallized from ethanol to give 1-methyl-4-phenyl-1,2,5,6,7,8-hexahydrobenzothieno[ 2,3-d]pyrimidin-2-one as crystals having a melting point of 215° - 216°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 and residue
  6. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-6a25fd88cea046c0ac8632b1f96a97f8
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

Loading…