Benzoyl chloride → HCID 22499210, compound

HRID 577636Notes

Reaction equation

HRID 577636 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([CH3:22])=[C:16]2[C:12]=1[CH2:13][C:14](=[N:24]O)[C:15]2=[O:23].C(N(CC)CC)C>ClCCl>[CH3:10][C:11]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:17]([CH3:22])=[C:16]2[C:12]=1[CH2:13][CH:14]([NH:24][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:15]2=[O:23]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 73187799HCID 73187799, compound

Product 1

HCID 22499210HCID 22499210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (1.635 g) is added dropwise to 4,5,6,7-tetramethyl-indan-1,2-dione 2-oxime (2.53 g) and triethylamine (2.25 g) in anhydrous dichloromethane (60 ml) at 0° C. The reaction mixture is stirred at room temperature for 1.5 hours after which the solid product is filtered off and allowed to stir with water (150 ml), refiltered and dried. The organic filtrate is washed with 1M HCl, 10% brine, saturated sodium bicarbonate solution, 10% brine and treated with magnesium sulphate. After filtration, the solvent is removed in vacuo and the product triturated with diethyl ether, filtered and dried.

Workup

  1. filtrationis filtered off
  2. stirringto stir with water (150 ml)
  3. customdried
  4. washThe organic filtrate is washed with 1M HCl, 10% brine, saturated sodium bicarbonate solution, 10% brine
  5. additiontreated with magnesium sulphate
  6. filtrationAfter filtration
  7. customthe solvent is removed in vacuo
  8. customthe product triturated with diethyl ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-1f3855b5d67e43deb0a11f94de722350
Source dataset
uspto-grants-2015_05
Patent number
US09040559B2

Reaction notes

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