Methyl iodide → N-methyl-N-acetyl-2-(benzylthio)acetamide

HRID 1065307Notes

Reaction equation

HRID 1065307 reaction equation
[C:1]([NH:4][C:5](=[O:15])[CH2:6][S:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH3:18][N:4]([C:1](=[O:3])[CH3:2])[C:5](=[O:15])[CH2:6][S:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12837900HCID 12837900, compound

Product 1

HCID 20540314N-methyl-N-acetyl-2-(benzylthio)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 11.15 g. (0.05 mole) of the product of Step A above in 75 ml. of dimethylformamide was cooled to -5° C. and there was then added 2.4 g. (0.05 mole) of 50% sodium hydride. The reaction mixture was aged for 30 minutes at -5° C., after which there was added 3.2 ml. (0.05 mole) of methyl iodide, and the reaction mixture was aged for 1 hour, 15 minutes at 0° C. and 45 minutes at room temperature. The reaction mixture was poured into ice water, seeded and placed in a refrigerator overnight. It was then filtered, washed with water and air dried. A yield of 9.0 g. of product was obtained.

Workup

  1. additionthere was then added 2.4 g
  2. additionafter which there was added 3.2 ml
  3. customplaced in a refrigerator overnight
  4. filtrationIt was then filtered
  5. washwashed with water and air
  6. customdried
  7. customof product was obtained

Sources & evidence

ORD record
ord-99638db8cc5c46d39831836e1f12c985
Source dataset
uspto-grants-1982_05
Patent number
US04329363

Reaction notes

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