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

HRID 2274012Notes

Reaction equation

HRID 2274012 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178509332CID 101611454CatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-946cc60b37e244af9d34224f11fde5de
Source dataset
uspto-grants-2015_09
Patent number
US09126945B2

Reaction notes

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