Dimethylformamide → Chlorfenapyr

HRID 1708591

Reaction equation

HRID 1708591 reaction equation
[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[CH2:20]([O:22][CH2:23]OCC)[CH3:21].CN(C)C=O.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:5]([CH2:23][O:22][CH2:20][CH3:21])[C:6]=1[C:7]([F:10])([F:9])[F:8]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10024DiethoxymethaneHCID 24813Phosphorus oxychlorideHCID 183559Tralopyril

Product 1

HCID 91778ChlorfenapyrYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

A stirred mixture of 4-bromo-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (17.4 g, 0.05 mole), diethoxymethane (10.4 g, 0.10 mole) and dimethylformamide (DMF) (4.6 g, 0.0625 mole) in toluene, under N2, is treated portion-wise with phosphorous oxychloride (9.6 g, 0.0625 mole) at 35°-45° C. over a 10 minute period, heated at 45°-53° C. for about 0.5 hour, cooled to 35° C. and treated dropwise with triethylamine (7.25 g, 0.0715 mole) over a 2 hour period at 35°-45° C. The reaction mixture is treated with water and the toluene is removed via azeotropic distillation. The remaining residue is treated with water, filtered and the filtercake is dried in vacuo at 60° C. to give the title product, 20.8 g, 92.7% pure, 94.6% yield, identified by HPLC analysis.

Workup

  1. temperatureheated at 45°-53° C. for about 0.5 hour
  2. customthe toluene is removed via azeotropic distillation
  3. additionThe remaining residue is treated with water
  4. filtrationfiltered
  5. customthe filtercake is dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-06272aa97ad144cc9ba7983b6d33c56a
Source dataset
uspto-grants-1994_10
Patent number
US05359090

Linked notes

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