Ethanol → HCID 13207879, compound

HRID 918247Notes

Reaction equation

HRID 918247 reaction equation
[C:1]12([CH2:11][NH:12][C:13]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:14]=3[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:30](=[O:35])(OCC)[NH2:31].C(O)C>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)Cl>[C:1]12([CH2:11][N:12]3[C:13]4[C:14](=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=4)[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:31][C:30]3=[O:35])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 3

HCID 702EthanolHCID 5641Carbamic acid, ethyl esterHCID 21521530HCID 21521530, compound

Product 1

HCID 13207879HCID 13207879, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 3.9 g of 2-(1-adamantylmethyl-amino)-5-nitrobenzophenone, 6.4 g of ethyl carbamate and 0.45 g of anhydrous zinc chloride was heated at 170°- 180°C for 1 hour, and then, distillating off the produced ethanol, heating was continued at that temperature for additional 1 hour. After cooling, chloroform was added thereto and insoluble material was filtered off. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residual oil was chromatographed on silica gel using chloroform as eluting solvent to give 1-(1-adamantylmethyl)-4-phenyl-6-nitro-2(1H)-quinazolinone, m.p. 230°- 233°C, following recrystallization from a mixture of ethanol and chloroform.

Workup

  1. temperaturewas heated at 170°- 180°C for 1 hour
  2. temperatureheating
  3. temperatureAfter cooling
  4. filtrationinsoluble material was filtered off
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residual oil was chromatographed on silica gel
  9. washas eluting solvent

Sources & evidence

ORD record
ord-f3fc40424b9344b498fab6c9f66a366d
Source dataset
uspto-grants-1976_07
Patent number
US03970654

Reaction notes

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