Anthranilamide → HCID 5076882, compound

HRID 248835Notes

Reaction equation

HRID 248835 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:8]([NH2:17])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[O:6]=[C:1]([NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[C:8]([NH2:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 6942AnthranilamideHCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 5076882HCID 5076882, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Valeryl chloride (6.0 mL, 50 mmol) was added to a mixture of anthranilamide (6.8 g, 50 mmol) and triethylamine (7.0 mL, 50 mmol ) in tetrahydrofuran (100 mL) at 25° C. A rapid, exothermic reaction was observed, but no external cooling was required to prevent reflux. The mixture was stirred at ambient temperature for 19 hours, after which it was poured into excess aqueous sodium bicarbonate solution, extracted with ethyl acetate, dried (magnesium sulfate), and concentrated in vacuo. The residue was triturated with hexane/ether to give the title compound as a tan solid (9.9 g, 90%); m.p. 119°-120° C.

Workup

  1. customA rapid, exothermic reaction
  2. temperatureno external cooling
  3. temperatureto prevent reflux
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with hexane/ether

Sources & evidence

ORD record
ord-7a58ac5630654e6cb517bad98c95e817
Source dataset
uspto-grants-1993_05
Patent number
US05212177

Reaction notes

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