3'-Aminoacetophenone → HCID 69708144, compound

HRID 395374Notes

Reaction equation

HRID 395374 reaction equation
[CH3:1][S:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)=[O:12]>>[CH3:1][S:2][C:3]([NH:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:11](=[O:12])[CH3:10])[CH:14]=1)=[CH:4][N+:5]([O-:7])=[O:6]

Participants

3

Reactant 2

HCID 74173'-AminoacetophenoneHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 69708144HCID 69708144, compoundYield 65%

Conditions

Temperature
140 °C

Procedure

A neat mixture of 1,1-bismethylthio-2-nitroethylene (6.5 g, 38.5 mmol, 10 eq) and 3-aminoacetophenone (0.5 g, 3.85 mmol, 1 eq) was melted together and heated at 140° C. for four hours. The mixture was cooled to room temperature, then subjected to flash chromatography, eluting with 50% ethyl acetate/hexanes, to yield 0.63 g of a yellow powder as product. Yield=65%. NMR (300 MHz, CDCl3) δ 11.82 (bs, 1H), 7.95-7.91 (m, 2H), 7.59-7.48 (m, 2H), 6.73 (s, 1H), 2.65 (s, 3H), 2.41 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washeluting with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e16f10c1ce0744bdbf26eb7cff9619a3
Source dataset
uspto-grants-2003_08
Patent number
US06605623B1

Reaction notes

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