Ethyl Acetate → HCID 15296960, compound

HRID 374516Notes

Reaction equation

HRID 374516 reaction equation
[CH2:1]([O:3][CH2:4]Cl)[CH3:2].[Br:6][C:7]1[C:8]([C:24]#[N:25])=[C:9]([C:16]2[S:17][C:18]([Cl:23])=[C:19]([Cl:22])[C:20]=2[Cl:21])[NH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O.CCCCCC>[Br:6][C:7]1[C:8]([C:24]#[N:25])=[C:9]([C:16]2[S:17][C:18]([Cl:23])=[C:19]([Cl:22])[C:20]=2[Cl:21])[N:10]([CH2:4][O:3][CH2:1][CH3:2])[C:11]=1[C:12]([F:13])([F:15])[F:14]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 15296959HCID 15296959, compound

Product 1

HCID 15296960HCID 15296960, compoundYield 7,005.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Chloromethyl ethyl ether (0.20 g, 2.13 mmol) is added to a mixture of 4-bromo-2-(3,4,5-trichloro-2-thienyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (0.30 g, 0.71 mmol) and potassium carbonate (0.29 g, 2.13 mmol) in N,N-dimethylformamide. The reation mixture is stirred at room temperature for 30 minutes, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to obtain a clear oil. Flash chromatography of the oil using silica gel and a 15% ethyl acetate in hexane solution gives the title product as white crystals (0 24 g, 71%, mp 85°14 87° C.)

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts are washed sequentially with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto obtain a clear oil

Sources & evidence

ORD record
ord-a7bd45c31ba1451ea5d18d6358d5dd3a
Source dataset
uspto-grants-1996_01
Patent number
US05480902

Reaction notes

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