Acetamide → HCID 9946362, compound

HRID 1884345Notes

Reaction equation

HRID 1884345 reaction equation
[CH2:1]([CH:3]([CH2:25][CH3:26])[CH2:4][C:5]1[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[C:6]=1[NH:21][C:22](=O)[CH3:23])[CH3:2].[Cl-].[NH4+].C([NH2:32])(=O)C>>[CH2:1]([CH:3]([C:4]1[C:5]2[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:6]=2[N:21]=[C:22]([CH3:23])[N:32]=1)[CH2:25][CH3:26])[CH3:2]

Participants

4

Reactant 3

HCID 178AcetamideHCID 25517Ammonium ChlorideHCID 23505752HCID 23505752, compound

Product 1

HCID 9946362HCID 9946362, compoundYield 59.3%

Procedure

A mixture of N-[3-(2-ethyl-butyl )4,5-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrrol-2-yl]-acetamide (100 mg, 0.27 mmol), ammonium chloride (290 mg, 5.42 mmol), and acetamide (1.635 g) was heated to reflux for 2 hours. The mixture was cooled, quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 56 mg of the title compound as a dark oil. The oil was purified through silica gel column chromatography to give the title compound as a yellow oil. 1H-NMR (CDCl3) δ 0.85(t, 6H), 1.70-2.0(m, 4H), 1.83(s, 6H), 1.99(s, 3H), 2.36(s, 3H), 2.44(s, 3H), 2.61 (s, 3H), 3.26(m, 1H), 7.00(s, 2H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6227f7577ce044739f6294ca13461bf8
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

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