Benzaldehyde → HCID 21411641, compound

HRID 2071588Notes

Reaction equation

HRID 2071588 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:5]([NH2:7])=[O:6].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>[Cl-].[Zn+2].[Cl-].C1(C)C(C)=CC=CC=1>[F:1][C:2]([F:16])([F:17])[CH2:3][N:4]1[C:8]2[C:13](=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:7][C:5]1=[O:6]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 21411642N-(4-Methoxyphenyl)-N-(2,2,2-trifluoroethyl)urea

Product 1

HCID 21411641HCID 21411641, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 3.23 g (0.013 mole) of N-(2,2,2-trifluoroethyl)-N-(p-methoxyphenyl)urea, 1.6 g (0.015 mole) of benzaldehyde, 5.3 g (0.039 mole) of anhydrous zinc chloride, and 65 ml of xylene was stirred for a while and then heated under reflux for 15 hours, removing the water formed azeotropically. Thereafter, 20 ml of 1N-hydrochloric acid was added to the reaction mixture and the mixture was stirred for a while. The organic layer was separated from the reaction mixture, washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The resulting residue was treated with isopropyl alcohol to give 2.71 g (62%) of 1-(2,2,2-trifluoroethyl)-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinone, m.p. 168°-169° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. customremoving the water
  4. customformed azeotropically
  5. stirringthe mixture was stirred for a while
  6. customThe organic layer was separated from the reaction mixture
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure
  10. additionThe resulting residue was treated with isopropyl alcohol

Sources & evidence

ORD record
ord-e6b5d42d76d542e78b394dcda1fbe5dc
Source dataset
uspto-grants-1977_09
Patent number
US04048168

Reaction notes

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