Triethylamine → HCID 67494092, compound

HRID 1968930Notes

Reaction equation

HRID 1968930 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([NH:8][C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=CN=2)[CH:7]=1.[CH2:20]([N:22](CC)CC)C.[CH3:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:19][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:28]([CH3:27])=[CH:29][CH:30]=2)=[CH:7][C:6]=1[NH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]1[CH:20]=[N:22][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 134054-Methylbenzoyl ChlorideHCID 86664945HCID 86664945, compound

Product 1

HCID 67494092HCID 67494092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of step 3 (0.25 g) and triethylamine (0.2 ml) in dichloromethane (25 ml), a solution of 4-methylbenzoyl chloride (0.5 g) in dichloromethane (10 ml) was added dropwise slowly in an ice-bath with the temperature no more than 5° C. After addition, the reaction was carried out for to 30 min in an ice-bath, and then at room temperature overnight. The completion of reaction was indicated by TLC. After that potassium carbonate solution (10%) was added, and then a solid was precipitated, and filtered out. The filter cake was washed with water, and recrystallized from ethyl acetate to give a solid.

Workup

  1. additionAfter addition
  2. customthe reaction was carried out for to 30 min in an ice-bath
  3. customat room temperature
  4. customovernight
  5. customThe completion of reaction
  6. customa solid was precipitated
  7. filtrationfiltered out
  8. washThe filter cake was washed with water
  9. customrecrystallized from ethyl acetate
  10. customto give a solid

Sources & evidence

ORD record
ord-eedb9b2f82144a73bfd75213a84c032e
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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