Water → HCID 23326335, compound

HRID 1380274Notes

Reaction equation

HRID 1380274 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[C:2]#[CH:3].[OH2:18].[K+].[Br-]>N1C=CC=CC=1CO.CC([O-])=O.CC([O-])=O.[Cu+2].O>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([NH:4][CH2:1][C:2]#[C:3][C:3]#[C:2][CH2:1][NH:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=2[C:14]([F:15])([F:16])[F:17])=[C:6]([C:14]([F:15])([F:16])[F:17])[CH:7]=1)([O-:12])=[O:18]

Participants

6

Reactant 3

HCID 962WaterHCID 253877Potassium BromideHCID 23326338HCID 23326338, compound

Product 1

HCID 23326335HCID 23326335, compound

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 11474PiconolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of Cu(OAc)2.H2O (4.5 g) in pyridinemethanol (1:1, 30 ml) was added N-(2-propynyl)-4-nitro-2-trifluoromethylaniline (3.01 g, 1.23×10-1 mole). The reaction mixture was stirred at 50° C. for two hours. The mixture was poured into excess water and filtered. The crude solid was recrystallized from nitromethane to afford pale pink crystals. Yield: 2.54 g (84%). The material does not melt below 200° C. but turns dark red at 135° C. I.R. (KBr): 3405 (NH), 1580 (Ar-NO2) and 1290 cm-1 (CF3).

Workup

  1. filtrationfiltered
  2. customThe crude solid was recrystallized from nitromethane
  3. customto afford pale pink crystals
  4. customdoes not melt below 200° C.
  5. customat 135° C

Sources & evidence

ORD record
ord-8b94ed2bd5e24c2a986af8cbc74bc3b8
Source dataset
uspto-grants-1986_04
Patent number
US04581315

Reaction notes

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