Benzoyl chloride → HCID 23293551, compound

HRID 1954696Notes

Reaction equation

HRID 1954696 reaction equation
Cl.[NH2:2][CH:3]([CH3:19])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C([O-])(O)=O.[Na+].[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OC(C)C)(C)C>C(Cl)(Cl)Cl.C1COCC1.O>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([CH:4]([C:5]2[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=2)[CH:3]([NH:2][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:19])=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 7914Diisopropyl EtherHCID 516892Sodium BicarbonateHCID 85718914HCID 85718914, compound

Product 1

HCID 23293551HCID 23293551, compoundYield 80.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 12 (5.00 g, 17.0 mmol) was dissolved in chloroform (70 mL), THF (30 mL), and 50 mL saturated aqueous NaHCO3 solution. The reaction mixture was treated with benzoyl chloride (2.5 mL, 21.5 mmol) and the water (25 mL). The reaction mixture was stirred for 5 days. The organic phase was collected, dried (MgSO4), and filtered. The filtrate was concentrated. The residue obtained was dissolved in hot THF and diisopropylether was added until a slight cloudiness developed. The solid which formed on cooling was collected by filtration, washed with additional diisopropylether, and dried under vacuum to give the title compound (4.78 g, 77%) as a white solid.

Workup

  1. customThe organic phase was collected
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customThe residue obtained
  6. customThe solid which formed
  7. temperatureon cooling
  8. filtrationwas collected by filtration
  9. washwashed with additional diisopropylether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-f4617dd1d6af4a7b9d2bbd9a6e0f73d6
Source dataset
uspto-grants-2000_09
Patent number
US06124280

Reaction notes

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