Iodoethane → HCID 54030285, compound

HRID 1634088Notes

Reaction equation

HRID 1634088 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]2)=[CH:4][CH:3]=1.[CH2:21](I)[CH3:22].CC[N:26](C(C)C)C(C)C>CN(C)C=O.O>[F:20][C:17]([F:18])([F:19])[C:10]1[CH:11]=[C:12]([C:13]([F:14])([F:15])[F:16])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:21][CH2:22][NH2:26])=[CH:3][CH:4]=2)[N:9]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 54030285HCID 54030285, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(4′-aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.15 g, 0.58 mmol), ethyl iodide (0.10 mL, 1.26 mmol), and Hunig's base (0.20 mL, 1.14 mmol) in N,N-dimethylformamide (10 mL) was heated to 50° C. under argon with stirring. After 24 hours the mixture was diluted with water, and extracted with ethyl acetate. The organic phase was washed with water (4×25 mL), brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography (ethyl acetate/hexanes) followed by recrystallization from ethanol/water to give the above-named compound (0.045 g) as yellow crystals. mp 54° C. NMR (CDCl3, 400 MHz): δ 7.26 (d, 2H), 7.02 (s, 1H), 6.64 (d, 2H), 3.93 (br s, 1H), 3.22 (q, 2H), 1.31 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water (4×25 mL), brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (ethyl acetate/hexanes)
  6. customfollowed by recrystallization from ethanol/water

Sources & evidence

ORD record
ord-ec5264bfbc9649ffa642d5676b51c1f5
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

Loading…