Methyl iodide → HCID 13457751, compound

HRID 280125Notes

Reaction equation

HRID 280125 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[N:7]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:8]=[CH:9][CH:10]=1)=[O:5].[C:21](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[N:7]([N:11]([CH3:21])[C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:8]=[CH:9][CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 13457750HCID 13457750, compound

Product 1

HCID 13457751HCID 13457751, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[2-(2-Chlorobenzoyl)-1H-pyrrol-1-yl]-carbamic acid, ethyl ester (22 g, 75.1 mmol), sodium carbonate (16.0 g, 0.112 mol) and methyl iodide (13 g, 0.122 mol) were added to 100 ml of dry DMF and the mixture stirred at ambient temperature for 78 hours. The reaction was quenched with 1 liter of H2O and extracted with five 200 ml portions of diethyl ether. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and evaporated to give 15 g of solid. This solid was purified by HPLC (silica gel, DCM) to give 13.1 g (57%) of crystals, m.p. 54°-56°.

Workup

  1. customThe reaction was quenched with 1 liter of H2O
  2. extractionextracted with five 200 ml portions of diethyl ether
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-63071b00f20f475e8ee901ff7381bf22
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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