Dimethylformamide → Chlorfenapyr

HRID 1708591

반응식

HRID 1708591 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 91778Chlorfenapyr수율 94.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
35 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-06272aa97ad144cc9ba7983b6d33c56a
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05359090

연결된 노트

불러오는 중…