Methyl iodide → HCID 18991991, compound

HRID 375750Notes

Reaction equation

HRID 375750 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:25]=[CH:24][C:8]2[O:9][C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)=[O:4].[CH2:26]([Li])CCC.CI.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][NH:2][C:3]([C:5]1[CH:25]=[CH:24][C:8]2[O:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:11][C:7]=2[C:6]=1[CH3:26])=[O:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 18992010HCID 18992010, compoundHCID 178418339Butyllithium

Product 1

HCID 18991991HCID 18991991, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 3.30 g of N-methyl-2,2-diphenyl-1,3-benzodioxole-5-carboxamide in 20 ml of tetrahydrofuran, cooled to -78° C., were added 12.5 ml of a 1.6M solution of n-butyllithium in hexane. The solution was stirred for 1 hour, the temperature being allowed to warm up to 20° C. Then, 1.37 g of methyl iodide were added, and stirring was continued for 1 hour. After the addition of 20 ml saturated ammonium chloride solution, the mixture was extracted with ethyl acetate. The organic layer was washed successively with 2N potassium hydrogensulfate solution, saturated potassium bicarbonate solution and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the solid residue was crystallized from ethanol to give 15.6 g of N, 4-dimethyl-2,2-diphenyl-1,3-benzodioxole-5-carboxamide, m.p. 178°-180° C.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with 2N potassium hydrogensulfate solution, saturated potassium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe solid residue was crystallized from ethanol

Sources & evidence

ORD record
ord-7c8daf5a30be415f8a92a4737054a5dd
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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