Benzoyl chloride → HCID 86627417, compound

HRID 1686152Notes

Reaction equation

HRID 1686152 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[CH:6]=1.CCN(CC)CC.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[Br:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][O:13][C:7]1[CH:6]=[C:5]([CH:12]=[CH:11][C:8]=1[CH:9]=[O:10])[O:4][CH2:3][CH2:2][NH:1][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86627418HCID 86627418, compound

Product 1

HCID 86627417HCID 86627417, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Aminoethoxy)-2-(2-bromobenzyloxy)benzaldehyde (200 mg, 0.43 mmol) was dissolved in CH2Cl2 (20 ml) and Et3N (87.02 mg, 0.12 ml, 0.86 mmol) was added to the solution, followed by stirring for 2˜3 min. Benzoyl chloride (60.45 mg, 50 μl, 0.43 mmol) was also added before additionally stirring at room temperature for 2 hours. After completion of the reaction, the reaction solution was extracted with brine and CH2Cl2 (×3). The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in a vacuum. The residue was purified using column chromatography (ethyl acetate/n-hexane=1/5→1/3) to afford the object compound (white solid, 78 mg, 40%).

Workup

  1. stirringbefore additionally stirring at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction solution was extracted with brine and CH2Cl2 (×3)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in a vacuum
  7. customThe residue was purified
  8. customto afford the object compound (white solid, 78 mg, 40%)

Sources & evidence

ORD record
ord-fe14dd9cf995435f827a2ee6df78eca7
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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