2-Propanol, reaction products with ammonia, distn. residues → HCID 22136465, compound

HRID 1827260Notes

Reaction equation

HRID 1827260 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([C:7]1[CH:12]=[C:11]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH:22][C:23](=O)[CH3:24])=O.[NH3:29].CC(O)C>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([C:11]2[CH:12]=[C:7]3[C:8](=[CH:9][CH:10]=2)[N:22]=[C:23]([CH3:24])[N:29]=[C:5]3[C:4]2[CH:26]=[CH:27][CH:28]=[C:2]([Cl:1])[CH:3]=2)=[O:21])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 21578661N-[2-(3-Chlorobenzoyl)-4-(4-chlorobenzoyl)phenyl]acetamide

Product 1

HCID 22136465HCID 22136465, compoundYield 36%

Procedure

A mixture of N-[2-(3-chlorobenzoyl)-4-(4-chlorobenzoyl)phenyl]acetamide (0.008 mol), described in International Patent Specification WO97/16443, in NH3/iPrOH (4.5M) (17 ml) was stirred at 160° C. for 6 hours in a small bomb, cooled, poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc 80/20; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue (1.2 g) was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 1.13 g (36%) of (4-chlorophenyl)[4-(3-chlorophenyl)-2-methyl-6-quinazolinyl]-methanone, mp. 182° C. (intermediate 4).

Workup

  1. temperaturecooled
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc 80/20; 15–40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue (1.2 g) was crystallized from diethyl ether
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-8b38e2c6798a4f83bf9ec727fb85ccc6
Source dataset
uspto-grants-2006_05
Patent number
US07053105B2

Reaction notes

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