Methyl iodide → HCID 53888452, compound

HRID 1606149Notes

Reaction equation

HRID 1606149 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([C:10]2[N:14]([CH3:15])[C:13]([CH2:16][C:17]#[N:18])=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1.[CH3:21]I>COCCOC>[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([C:10]2[N:14]([CH3:15])[C:13]([CH:16]([CH3:21])[C:17]#[N:18])=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18424281HCID 18424281, compound

Product 1

HCID 53888452HCID 53888452, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of sodium hydride (12.2 g. of 50% w/w Nah in mineral oil) in 1,2-dimethoxyethane is added 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetonitrile (62.6 g., 0.24 mole) in 1,2-dimethoxyethane over a period of 1/2 hr. at room temperature. After the addition is complete, the mixture is stirred for 1 hour and then 35 g. (0.25 mole) of methyl iodide is added. The reaction mixture is stirred for an additional 3 hrs., concentrated under reduced pressure, diluted with water and extracted with chloroform. After drying, the chloroform is removed leaving a brown solid residue which is triturated with cold methanol to give yellow crystals of 5-(p-chlorobenzoyl)-α-methyl-1-methylpyrrole-2-acetonitrile, m.p. 145°-148°C. Two recrystallizations from methanol raises the m.p. to 151.5°-152.5°C.

Workup

  1. customat room temperature
  2. additionAfter the addition
  3. stirringThe reaction mixture is stirred for an additional 3 hrs
  4. concentration, concentrated under reduced pressure
  5. additiondiluted with water
  6. extractionextracted with chloroform
  7. customAfter drying
  8. customthe chloroform is removed
  9. customleaving a brown solid residue which
  10. customis triturated with cold methanol

Sources & evidence

ORD record
ord-f9c62154fcd045ddbf5c6b808c8e1910
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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