Methane → HCID 57108014, compound

HRID 266552Notes

Reaction equation

HRID 266552 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH:17]1([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH2:21])[CH2:19][CH2:18]1.C(N(CC)CC)C.C>C1(C)C=CC=CC=1>[CH:17]1([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:21][C:6]([C:5]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])=[O:7])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 143235242-Nitro-4-(trifluoromethyl)benzoyl chlorideHCID 53912938HCID 53912938, compound

Product 1

HCID 57108014HCID 57108014, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-nitro-4-trifluoromethylbenzoyl chloride (9.4 g) was added dropwise to a cooled mixture of 1-cyclopropyl-1-diethylaminoethene (5.1 g) and triethylamine (3.7 g) in toluene (100 ml) whilst maintaining the temperature below 10° C. The mixture was then stirred at room temperature for 1 hour. The suspension was treated with decolourising charcoal and filtered. The filtrate was evaporated and the residue was purified by chromatography on silica gel eluted with a mixture of ethyl acetate and dichloromethane (1:9) to give 3-cyclopropyl-3-diethylamino-1-(2-nitro-4-trifluoromethylphenyl)-prop-2-en-1-one (4.1 g) as a red oil with its 1H NMR (in CDCl3) giving peaks at d=0.7-1.8(m, 11H), 3.5(q, 4H), 5.0(s, 1H), 7.5(d, 1H), 7.7(d, 1H),and 7.95(s, 1H).

Workup

  1. temperaturewhilst maintaining the temperature below 10° C
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue was purified by chromatography on silica gel
  5. washeluted with a mixture of ethyl acetate and dichloromethane (1:9)

Sources & evidence

ORD record
ord-0e52b84397624ce295f50e5e6e9dc26e
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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