N-Ethylaniline → HCID 58696273, compound

HRID 1178341Notes

Reaction equation

HRID 1178341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:23][CH3:24])([CH2:20][CH:21]=[CH2:22])[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[CH2:13][C:14]([F:17])([F:16])[F:15])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)C(C)C)(C)C.[C:34](Cl)(=[O:38])[C:35](Cl)=[O:36].[CH2:40]([NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH3:41]>C(Cl)Cl.O>[F:15][C:14]([F:16])([F:17])[CH2:13][C:12]([N:11]([CH2:10][C@@:9]([N:23]([CH3:24])[C:34](=[O:38])[C:35]([N:42]([CH2:40][CH3:41])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:36])([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:20][CH:21]=[CH2:22])[CH3:19])=[O:18]

Participants

7

Reactant 4

HCID 7670N-EthylanilineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 58696249HCID 58696249, compound

Product 1

HCID 58696273HCID 58696273, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-[2-(S)-(3,4-Dichlorophenyl)-2-(methylamino)-4-pentenyl]-3,3,3-trifluoro-N-methylpropanamide (200 mg) was dissolved in anhydrous methylene chloride (1 mL). Under cooling with ice, N,N-diisopropylethylamine (109 μL) and oxalyl chloride (109 μL) were added thereto, and the mixture was stirred for 30 minuites. A solution of N-ethylaniline (127 mg) in anhydrous methylene chloride (1 mL) was added to the reaction mixture, and the resultant mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture, extracted with methylene chloride, washed with saturated brine, and dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=3:1 to 1:1), to thereby give the title compound (221 mg, 75.8%).

Workup

  1. additionwere added
  2. extractionextracted with methylene chloride
  3. washwashed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-59a6d8eb66e54e59ba1c3b8ccac2114e
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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