Methyl iodide → HCID 13457736, compound

HRID 280119Notes

Reaction equation

HRID 280119 reaction equation
[C:1]([C:9]1[N:10]([NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])[CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](=O)([O-])[O-].[Na+].[Na+].CI>CN(C)C=O>[C:1]([C:9]1[N:10]([N:14]([CH3:20])[C:15](=[O:19])[O:16][CH2:17][CH3:18])[CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 13457734HCID 13457734, compound

Product 1

HCID 13457736HCID 13457736, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Benzoyl-1H-pyrrol-1-yl)-carbamic acid, ethyl ester (18.5 g, 71.6 mmol) was combined with sodium carbonate (16.0 g, 157 mmol) and methyl iodide (13.2 g, 93 mmol) in 100 ml of dimethylformamide. The resulting slurry was stirred at ambient temperature for 20 hours and then at 75° C. for 2 hours. This reaction mixture was poured into 300 ml of crushed ice and extracted with four 200 ml portions of ether. The combined extracts were washed with water, dried over MgSO4, filtered and evaporated to an oil which was purified by HPLC (silica gel, 15% hexane/DCM). The resulting material was recrystallized from ether-hexane to give 18.4 g (94%) of cubes, m.p. 50°-52°.

Workup

  1. waitat 75° C. for 2 hours
  2. extractionextracted with four 200 ml portions of ether
  3. washThe combined extracts were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customwas purified by HPLC (silica gel, 15% hexane/DCM)
  8. customThe resulting material was recrystallized from ether-hexane
  9. customto give 18.4 g (94%) of cubes, m.p. 50°-52°

Sources & evidence

ORD record
ord-81c8524342764516941625dc1879fbb0
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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