HCID 86608958, compound → HCID 68408133, compound

HRID 1710811Notes

Reaction equation

HRID 1710811 reaction equation
[CH3:1][Li].[NH2:3][C:4]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:5]=1[C:6](N(OC)C)=[O:7]>O1CCCC1.O>[NH2:3][C:4]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:5]=1[C:6](=[O:7])[CH3:1]

Participants

5

Reactant 2

HCID 86608958HCID 86608958, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68408133HCID 68408133, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At −78° C. a solution of methyl lithium (1.6M in diethyl ether, 25 ml, 40 mmol) was added dropwise to a solution of 2-amino-3,6-dichloro-N-methoxy-N-methyl-benzamide (2.5 g, 10 mmol) in tetrahydrofurane (100 ml). After complete addition, the reaction was warmed to r.t. The dark solution was stirred for 3 hours at room temperature. Under ice cooling 2N aqueous hydrochloride solution (25 ml) was added dropwise and stirred at r.t. for 30 minutes. The reaction was diluted with water, extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was purified by column chromatography (silica gel, solvent gradient n-heptan/ethyl acetate=3/7) to yield the title compound as an orange oil (0.59 g, 29%).

Workup

  1. additionAfter complete addition
  2. additionUnder ice cooling 2N aqueous hydrochloride solution (25 ml) was added dropwise
  3. stirringstirred at r.t. for 30 minutes
  4. extractionextracted twice with ethyl acetate
  5. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography (silica gel, solvent gradient n-heptan/ethyl acetate=3/7)

Sources & evidence

ORD record
ord-04206ae683d9403aacbe3e3ad6ad66bf
Source dataset
uspto-grants-2010_09
Patent number
US07790732B2

Reaction notes

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