Pyridine → HCID 13412531, compound

HRID 2200173Notes

Reaction equation

HRID 2200173 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].CCOC(C)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 13412531HCID 13412531, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add 4-chloro-3-(trifluoromethyl)aniline (1.0 g, 5.1 mmol) and pyridine (1.0 g, 12.8 mmol) in DCM (10 mL), stir well and cool to 0° C. Add phenyl chloroformate (1.04 g, 6.6 mmol) at 0° C. After addition, stir the reaction at room temperature for 1 hr. TLC (EtOAc:PE=1:2) shows the reaction is complete. Wash the organic layer with 1M HCl solution (20 mL) and brine (20 mL) respectively. Dry over anhydrous Na2SO4; concentrate under reduced pressure to give the target compound (1.16 g) which is used without further purification. MS: (M+1): 316.1.

Workup

  1. customat 0° C
  2. additionAfter addition
  3. stirringstir
  4. customthe reaction at room temperature for 1 hr
  5. washWash the organic layer with 1M HCl solution (20 mL) and brine (20 mL) respectively
  6. dry with materialDry over anhydrous Na2SO4
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-bdeaa34988f14202930ab204ab18aa8c
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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