Ethyl Acetate → HCID 15296960, compound

HRID 2396536Notes

Reaction equation

HRID 2396536 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 71%

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°-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-bae9f6db9bba4d1c9d1a7b9647cc4494
Source dataset
uspto-grants-1996_02
Patent number
US05492925

Reaction notes

Loading…