Water → [2-(2-Fluorobenzoyl)-1H-pyrrol-1-yl]-methyl-carbamic acid, ethyl ester

HRID 462756Notes

Reaction equation

HRID 462756 reaction equation
[C:1](=O)([O-])[O-].[Na+].[Na+].CI.[F:9][C:10]1[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=1[C:12]([C:14]1[N:15]([NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[CH:16]=[CH:17][CH:18]=1)=[O:13].O>CN(C=O)C>[F:9][C:10]1[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=1[C:12]([C:14]1[N:15]([N:19]([CH3:1])[C:20](=[O:24])[O:21][CH2:22][CH3:23])[CH:16]=[CH:17][CH:18]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 13457759[2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]carbamic acid, ethyl ester

Product 1

HCID 13457760[2-(2-Fluorobenzoyl)-1H-pyrrol-1-yl]-methyl-carbamic acid, ethyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium carbonate (22.4 g, 0.21 mol), methyl iodide (30 g, 0.21 mol), and [2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]-carbamic acid, ethyl ester (25.4 g, 0.09 mol) were combined in 100 ml of dry DMF with stirring at ambient temperature. After 72 hours, the mixture was poured into 800 ml of H2O and extracted with three 250 ml portions of DCM. The combined extracts were washed with H2O and brine, dried (MgSO4), filtered and evaporated to an oil. This oil was purified by HPLC (silica, DCM) to give 26 g (97%) of crystals, m.p. 64°-66°.

Workup

  1. extractionextracted with three 250 ml portions of DCM
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to an oil
  6. customThis oil was purified by HPLC (silica, DCM)

Sources & evidence

ORD record
ord-49119ba095644b3e8fa71673bd1b3495
Source dataset
uspto-grants-1985_05
Patent number
US04517195

Reaction notes

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