Hydrochloric Acid → N-[2-(chloromethyl)-4-cyanophenyl]-2,2,2-trifluoroacetamide

HRID 388379노트

반응식

HRID 388379 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[C:5]([CH3:16])[CH:4]=1)#[N:2].S(Cl)([Cl:20])(=O)=O.Cl>C(Cl)(Cl)(Cl)Cl>[Cl:20][CH2:16][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[NH:9][C:10](=[O:15])[C:11]([F:13])([F:12])[F:14]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 24648Sulfuryl chlorideHCID 58126830HCID 58126830, 화합물2회

생성물 1

HCID 86650575N-[2-(chloromethyl)-4-cyanophenyl]-2,2,2-trifluoroacetamide

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

In a round-bottomed flask N-(4-cyano-2-methylphenyl)-2,2,2-trifluoroacetamide (Intermediate 1, 19.37 g, 85 mmol), sulfuryl dichloride (27.6 ml, 340 mmol) and diphenylperoxyanhydride (1.028 g, 4.24 mmol) were heated in carbon tetrachloride (210 ml) at 100° C. for 3 h. The mixture was cooled to room temperature and then the reaction mixture was poured into 2M HCl (350 mL). The organic layer was then collected and the solvent was removed to give N-[2-(chloromethyl)-4-cyanophenyl]-2,2,2-trifluoroacetamide as an orange oil, (25.54 g) which was used in the next step without further purification. This oil was added to triphenylphosphine (26.2 g, 100 mmol) and the mixture was heated in toluene (300 ml) at 110° C. for 3 h. The mixture was cooled to room temperature overnight and the precipitate was filtered and washed with small amounts of toluene and diethyl ether to give the title compound as an off-white solid (29.91 g);

후처리

  1. customThe organic layer was then collected
  2. customthe solvent was removed

출처 및 근거

ORD 기록
ord-b5658a236c3c478fb3b9c7075fddf35a
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377941B2

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