2-Amino-5-(trifluoromethyl)benzoic acid → 1-ethyl-7-trifluoromethyl-2,3-dihydro-imidazo[2.1-b]quinazolin-5(1H)-one

HRID 544546Notes

Reaction equation

HRID 544546 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][N:5]=[C:4]1SC)[CH3:2].[NH2:10][C:11]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:12]=1[C:13](O)=[O:14]>CC(N(C)C)=O>[CH2:1]([N:3]1[C:4]2=[N:10][C:11]3[C:12]([C:13](=[O:14])[N:5]2[CH2:6][CH2:7]1)=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=3)[CH3:2]

Participants

4

Reactant 2

HCID 104655352-Amino-5-(trifluoromethyl)benzoic acidHCID 125044921-Ethyl-2-(methylsulfanyl)-4,5-dihydro-1H-imidazole

Product 1

HCID 204582671-ethyl-7-trifluoromethyl-2,3-dihydro-imidazo[2.1-b]quinazolin-5(1H)-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 3.6 g. of 1-ethyl-2-methylthioimidazoline, 5.0 g. of 2-amino-5-trifluoromethylbenzoic acid and 50 ml. of dimethylacetamide is refluxed for 24 hours and then the reaction mixture concentrated in vacuo. The residue is dissolved in methylene chloride, washed first with 2 N sodium hydroxide solution and then with water, dried over magnesium sulfate, filtered and chromatographed on silica gel while eluding with methylene chloride to obtain 1-ethyl-7-trifluoromethyl-2,3-dihydro-imidazo[2.1-b]quinazolin-5(1H)-one.

Workup

  1. concentrationthe reaction mixture concentrated in vacuo
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washwashed first with 2 N sodium hydroxide solution
  4. dry with materialwith water, dried over magnesium sulfate
  5. filtrationfiltered
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-a7a673129f4148ee9f42d0da7402b3f3
Source dataset
uspto-grants-1984_05
Patent number
US04451464

Reaction notes

Loading…