Dimethylformamide → Chlorfenapyr

HRID 1708591

反応式

HRID 1708591 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

HCID 91778Chlorfenapyr収率 94.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
35 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-06272aa97ad144cc9ba7983b6d33c56a
出典データセット
uspto-grants-1994_10
特許番号
US05359090

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