Water → HCID 21411985, compound

HRID 2071681Notes

Reaction equation

HRID 2071681 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:19][C:20]#[N:21])[N:7]([CH3:18])[C:8]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.[CH3:22]I.O>COCCOC>[Cl:3][C:4]1[CH:5]=[C:6]([CH:19]([CH3:22])[C:20]#[N:21])[N:7]([CH3:18])[C:8]=1[C:9](=[O:17])[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21411896[4-Chloro-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetonitrile

Product 1

HCID 21411985HCID 21411985, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of 12.2g. of 50% sodium hydride (mineral oil) in 1,2-dimethoxyethane is added 70 g. (0.24 mole) of 4-chloro-5-(p-chlorobenzoyl)-1-methylpyrrole-2- acetonitrile in 1,2-dimethoxyethane over a period of one half hour at room temperature. After the addition is complete, the whole is stirred for one hour and then 35 g. (0.25 mole) of methyl iodide is added. The reaction mixture is stirred for an additional 3 hours and is concentrated in vacuo; the residue is diluted with water and extracted with chloroform. After the extract is dried the chloroform is removed, leaving a brown solid residue which, upon trituration with cold water, yields 4-chloro-5- (p-chlorobenzoyl)-α-methyl-1-methylpyrrole-2-acetonitrile.

Workup

  1. additionTo a suspension of 12.2g
  2. additionAfter the addition
  3. stirringThe reaction mixture is stirred for an additional 3 hours
  4. concentrationis concentrated in vacuo
  5. additionthe residue is diluted with water
  6. extractionextracted with chloroform
  7. dry with materialAfter the extract is dried the chloroform
  8. customis removed
  9. customleaving a brown solid residue which

Sources & evidence

ORD record
ord-6f615c451f7b48b982e5de19a42deea5
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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