Water → N-Butyl-N-(1-methyl-1H-pyrrol-2-yl)acetamide

HRID 372019Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[NH:7][C:8](=[O:10])[CH3:9].[H-].[Na+].[CH2:13](I)[CH2:14][CH2:15][CH3:16].O>CN(C)C=O>[CH2:13]([N:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)[C:8](=[O:10])[CH3:9])[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

N-(1-Methylpyrrol-2-yl)acetamide (3.20 g, 0.0231 mol) in dry dimethylformamide was maintained at a temperature less than 0° C, with stirring under nitrogen, during the slow addition of 50% sodium hydride/oil (1.11 g, 0.0231 mol). After the addition, the mixture was stirred at 0° C. for 30 minutes and then the temperature allowed to rise to 15° C. when n-butyl iodide (8.50 g, 0.0461 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 and the resulting oil distilled to give a colourless oil 3.72 g (83%) b.p. (airbath) 100° C/0.4 mm.

Workup

additionAfter the addition
customto rise to 15° C.
additionwas added
stirringThe mixture was stirred at room temperature overnight
extractionthe mixture extracted with ether (4 × 50 ml)
washThe combined extracts were washed with water (3 × 50 ml)
dry with materialdried over magnesium sulphate
customThe solvent was removed in vacuo
distillationthe resulting oil distilled

Sources & evidence

ORD record: ord-4fdd13a5cfd941c1a740dac186199ce8
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04088773

Reaction notes

Loading…