Water → N,2-Dimethyl-N-(1-methyl-1H-pyrrol-3-yl)propanamide

HRID 372020Notes

Reaction equation

HRID 372020 reaction equation
[CH3:1][CH:2]([CH3:12])[C:3]([NH:5][C:6]1[CH:10]=[CH:9][N:8]([CH3:11])[CH:7]=1)=[O:4].[H-].[Na+].I[CH3:16].O>CN(C)C=O>[CH3:16][N:5]([C:6]1[CH:10]=[CH:9][N:8]([CH3:11])[CH:7]=1)[C:3](=[O:4])[CH:2]([CH3:12])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 203533082-Methyl-N-(1-methyl-1H-pyrrol-3-yl)propanamide

Product 1

HCID 20353309N,2-Dimethyl-N-(1-methyl-1H-pyrrol-3-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-N-(1-methylpyrrol-3-yl)propanamide (2.50 g, 0.015 mol) in dry dimethylformamide (10 ml) was cooled to below 0° C. and stirred under nitrogen during the addition of 50% sodium hydride/oil (0.73 g, 0.0152 mol). After the addition, the mixture was stirred at 0° C. for 30 minutes and then brought to 15° C. when iodomethane (4.30 g, 0.0302 mol) was added. The mixture was stirred at room temperature overnight and then poured into water (200 ml) and the mixture extracted with ether (4 × 50 ml). The combined extracts were washed with water (3 × 50 ml) and dried over magnesium sulphate. The solvent was removed in vacuo to leave a solid which separated from pentane at -10° C as white flakes (2.11 g, 78%).

Workup

  1. additionAfter the addition
  2. custombrought to 15° C.
  3. additionwas added
  4. stirringThe mixture was stirred at room temperature overnight
  5. extractionthe mixture extracted with ether (4 × 50 ml)
  6. washThe combined extracts were washed with water (3 × 50 ml)
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent was removed in vacuo
  9. customto leave a solid which
  10. customseparated from pentane at -10° C as white flakes (2.11 g, 78%)

Sources & evidence

ORD record
ord-939e3d519c4742f0a43a14dc53db2663
Source dataset
uspto-grants-1978_05
Patent number
US04088773

Reaction notes

Loading…