Methyl iodide → HCID 86734983, compound

HRID 441366Notes

Reaction equation

HRID 441366 reaction equation
[CH3:1]I.[N+:3]([CH:6]([CH2:8][CH:9]([CH2:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:7])([O-:5])=[O:4].[OH-].[Na+]>CC(C)=O>[N+:3]([CH:6]([CH2:8][CH:9]([CH2:18][C:19]([N:21]([CH3:1])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:7])([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 86734982HCID 86734982, compound

Product 1

HCID 86734983HCID 86734983, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of methyl iodide (130 g) in acetone (160 ml) was added to a stirred mixture of 2-nitro-4-dodecylacetanilide (196 g) and sodium hydroxide (130 g) in acetone (1100 ml) at room temperature. The mixture was heated rapidly and allowed to boil for 8 minutes, filtered hot and the filtrate evaporated to a semi-solid which was partitioned between toluene (800 ml) and water (400 ml). The organic layer was washed with water, dried and evaporated to give 199 g of 2-nitro-4-dodecyl-N-methylacetanilide as a dark oil.

Workup

  1. temperatureThe mixture was heated rapidly
  2. filtrationfiltered hot
  3. customthe filtrate evaporated to a semi-solid which
  4. customwas partitioned between toluene (800 ml) and water (400 ml)
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-b534849038be465a913771fca970149b
Source dataset
uspto-grants-1977_08
Patent number
US04039612

Reaction notes

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