Water → N-(4-fluoro-3-nitrophenyl)thiophene-2-carboxamide

HRID 605273Notes

Reaction equation

HRID 605273 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(C(C)C)C(C)C.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](Cl)=[O:27].O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:26]([C:22]2[S:21][CH:25]=[CH:24][CH:23]=2)=[O:27])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 677684-Fluoro-3-nitroanilineHCID 789282-Thiophenecarbonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 771974N-(4-fluoro-3-nitrophenyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from 4-fluoro-3-nitro-phenylamine (2.00 g, 12.81 mmol) dissolved in THF (25 mL) and Hunig's base (3.312 g, 25.62 mmol) to which was added thiophene-2-carbonyl chloride (1.878 g, 12.81 mmol) drop wise over 10 minutes. Reaction mixture was stirred at room temperature for 1 hr at which time water was added and the title compound was collected by filtration (3.25 g, 95%).

Workup

  1. customReaction mixture
  2. additionwas added
  3. filtrationthe title compound was collected by filtration (3.25 g, 95%)

Sources & evidence

ORD record
ord-43fca7fff0d54fe781a3cf4b5258ab36
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…