Water → 5-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile

HRID 1666931Notes

Reaction equation

HRID 1666931 reaction equation
[OH-].[K+].[NH2:3][C:4]1[S:5][C:6]([CH3:11])=[CH:7][C:8]=1[C:9]#[N:10].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].O>C(#N)C>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:3][C:4]1[S:5][C:6]([CH3:11])=[CH:7][C:8]=1[C:9]#[N:10])([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 738951-Fluoro-2-nitrobenzeneHCID 6890562-Amino-5-methyl-3-thiophenecarbonitrile

Product 1

HCID 3954605-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrileYield 74.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Potassium hydroxide (101.4 g) in acetonitrile (150 ml) is taken under nitrogen and cooled to 0-5° C. A solution of 2-amino-5-methylthiophene-3-carbonitrile (100 g) and o-fluoronitrobenzene (122.6 g) in acetonitrile (550 ml) is added. The reaction is then stirred for 3 hours and chilled water is added. The solid thus obtained is filtered off and air-dried. The solid is crystallized from water-methanol mixture and the crystallized solid is dried under vacuum at 40-45° C. to obtain the title compound (140 g).

Workup

  1. additionis added
  2. customThe solid thus obtained
  3. filtrationis filtered off
  4. customair-dried
  5. customThe solid is crystallized from water-methanol mixture
  6. customthe crystallized solid is dried under vacuum at 40-45° C.

Sources & evidence

ORD record
ord-583fd1c771cd48b0a21c6fec945f5943
Source dataset
uspto-grants-2011_10
Patent number
US08044196B2

Reaction notes

Loading…