Carbamic acid, ethyl ester → HCID 21327522, compound

HRID 614914Notes

Reaction equation

HRID 614914 reaction equation
[CH2:1]([NH:7][C:8]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[C:25](=O)([O:27]CC)[NH2:26]>C(Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH2:1]([N:7]1[C:8]2[C:9](=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:26][C:25]1=[O:27])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 21327535HCID 21327535, compound

Product 1

HCID 21327522HCID 21327522, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 1.63 g of 2-tetrahydrofurfurylamino-5-nitrobenzophenone, 3.0 g of ethyl carbamate and 0.2 g of zinc chloride was heated at 190° C. (oil bath temperature) for 2 hours. After cooling, the reaction mixture was dissolved in chloroform and the insoluble material was filtered off. The chloroform solution was washed successively with dilute hydrochloric acid and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was washed with ether. The insoluble product was collected by filtration and dried to give 1-tetrahydrofurfuryl-4-phenyl-6-nitro-2(1H)-quinazolinone, m.p. 150°-152° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insoluble material was filtered off
  3. washThe chloroform solution was washed successively with dilute hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. washthe residue was washed with ether
  7. filtrationThe insoluble product was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-722ebf218d06467aa95a8d0fc68fc942
Source dataset
uspto-grants-1979_03
Patent number
US04146717

Reaction notes

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