Hydrochloric Acid → HCID 60207311, compound

HRID 1192052Notes

Reaction equation

HRID 1192052 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][NH:14][CH3:15].[CH2:16]=O.Cl>C(O)(C)C>[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH2:8][CH2:13][N:14]([CH3:16])[CH3:15])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one

Product 1

HCID 60207311HCID 60207311, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(5-chloro-4-nitro-2-thienyl)ethanone (1 g, 4.9 mmol) in isopropanol (20 mL), was added dimethylamine (0.55 g, 6.8 mmol) and paraformaldehyde (0.22 g, 7.3 mmol) and concentrated hydrochloric acid (0.2 mL). The resulting reaction mixture was heated at 80° C. for 18 hours. After this time, the reaction mixture was cooled to 0° C. and stirred at 0° C. for 1 hour. A pale yellow precipitate formed and collected by filtration to afford the corresponding hydrochloride salt of the title product (0.55 g, 38% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.39 (1H, m), 8.69 (1H, s), 3.68 (2H, m), 3.38 (2H, m), 2.80 (6H, s).

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter this time, the reaction mixture was cooled to 0° C.
  3. customA pale yellow precipitate formed
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f608357ec7fc4e8da758d4e727def918
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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