Dimethylformamide → HCID 11724470, compound

HRID 1708593Notes

Reaction equation

HRID 1708593 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[CH2:19]([O:21][CH2:22]OCC)[CH3:20].CN(C)C=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C(#N)C.O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:22][O:21][CH2:19][CH3:20])[C:10]([C:15]([F:18])([F:16])[F:17])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 10024DiethoxymethaneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 110001432-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 11724470HCID 11724470, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture of 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (13.5 g, 0.05 mole), diethoxymethane (7.8 g, 0.075 mole) and dimethylformamide (5.5 g, 0.075 mole) in acetonitrile, under N2, is treated with phosphorous oxychloride (11.5 g, 0.075 mole) over a 0.25 hour period at 39°-45° C., heated at 39°-45° C. for 0.75 hour and treated dropwise with triethylmine (10.1 g, 0.10 mole) at 45°-55° C. over a 0.5 hour period. The reaction mixture is diluted with water, stirred for 16 hours at 25° C. and concentrated in vacuo to give a crude product. The crude material is stirred at reflux temperature with a mixture of toluene and dilute aqueous NaOH and cooled to room temperature. The phases are separated and the organic phase is concentrated in vacuo to give the title product as a solid, mp 83°-84.5° C., 13.1 g, 80 % yield, identified by mass spectral analysis.

Workup

  1. temperatureheated at 39°-45° C. for 0.75 hour
  2. additiontreated dropwise with triethylmine (10.1 g, 0.10 mole) at 45°-55° C. over a 0.5 hour period
  3. concentrationconcentrated in vacuo
  4. customto give a crude product
  5. temperatureat reflux temperature
  6. temperaturecooled to room temperature
  7. customThe phases are separated
  8. concentrationthe organic phase is concentrated in vacuo

Sources & evidence

ORD record
ord-3b48b5fec29141bda01eb4085da1d10f
Source dataset
uspto-grants-1994_10
Patent number
US05359090

Reaction notes

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