4-tert-Butylbenzoyl chloride → HCID 20085630, compound

HRID 1608820Notes

Reaction equation

HRID 1608820 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)=[O:5].[C:18]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>CO.C(OCC)(=O)C>[NH:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[NH:1][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 743724-tert-Butylbenzoyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085630HCID 20085630, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 6B using 1.50 g (0.00651 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide, prepared as in Example 6A, and 2.61 g (0.01302 mol) of p-tert-butylbenzoyl chloride, with the exception that after reducing the initial reaction mixture to dryness, the resultant residue was dissolved in methanol and heated at reflux for 30 minutes. The methanol solution was then reduced to dryness under reduced pressure and the resultant residue was dissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated and the organic layer was washed with a saturated sodium chloride solution, dried with anhydrous sodium sulfate and reduced to dryness under reduced pressure to provide a yellow oil. This oil was purified by twice crystallizing the material from diethyl ether containing a small amount of ethyl acetate to provide 1.64 g of the desired titled compound (m.p. 127°-132° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. customreaction mixture to dryness
  3. temperatureheated
  4. temperatureat reflux for 30 minutes
  5. customThe resulting layers were separated
  6. washthe organic layer was washed with a saturated sodium chloride solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. customto provide a yellow oil
  9. customThis oil was purified
  10. customby twice crystallizing the material from diethyl ether containing a small amount of ethyl acetate

Sources & evidence

ORD record
ord-80496480d48a4fc483d775a2198e6c17
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

Loading…