Methyl 5-Amino-2-chlorobenzoate → methyl 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoate

HRID 2274012노트

반응식

HRID 2274012 반응식
[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[C:5]([C:10]([F:13])([F:12])[F:11])[C:4]([C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[N:3]1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:32])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28]>ClCCl.[Ag]C#N>[Cl:32][C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:14]([F:19])([F:20])[C:15]([F:17])([F:18])[F:16])[C:5]=2[C:10]([F:12])([F:13])[F:11])=[O:8])=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

참가 물질

5

반응물 2

HCID 5200412Methyl 5-Amino-2-chlorobenzoateHCID 866600741-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

생성물 1

HCID 86660079methyl 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoate

시약·촉매·용매 2

HCID 178509332CID 101611454촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4.24 g (12.8 mmol) of 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride in 25 ml of dichloromethane p.a. is added to a suspension of 2.38 g (12.8 mmol) of methyl 5-amino-2-chlorobenzoate and 2.57 g (19.2 mmol) of silver(I) cyanide in 50 ml of dichlormethane p.a., and the mixture is stirred at room temperature for 16 h. The suspension is then filtered through silica gel and the product is eluted using a mixture of cyclohexane and ethyl acetate (1:1). The organic phase is washed successively three times with 6N hydrochloric acid and twice with saturated sodium chloride solution. The organic phase is then dried over sodium sulphate, filtered and concentrated on a rotary evaporator under reduced pressure. This gives 5.75 g (93%) of methyl 2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)benzoate.

후처리

  1. filtrationThe suspension is then filtered through silica gel
  2. washthe product is eluted
  3. additiona mixture of cyclohexane and ethyl acetate (1:1)
  4. washThe organic phase is washed successively three times with 6N hydrochloric acid
  5. dry with materialThe organic phase is then dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator under reduced pressure

출처 및 근거

ORD 기록
ord-946cc60b37e244af9d34224f11fde5de
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126945B2

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