Pyridine → HCID 57974628, compound

HRID 2200188Notes

Reaction equation

HRID 2200188 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].N1C=CC=CC=1.C(Cl)Cl.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>CCOC(C)=O>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[C:6]([NH:7][C:23](=[O:24])[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 15891Phenyl chloroformateHCID 737533-(Trifluoromethoxy)aniline

Product 1

HCID 57974628HCID 57974628, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add 3-(trifluoromethoxy)aniline (1.0 g, 5.65 mmol), pyridine (0.89 g, 11.3 mmol) to DCM (20 mL) and cool to 0° C. Add dropwise phenyl chloroformate (1.15 g, 7.34 mmol). After addition, stir for 1 hr. TLC (PE:EtOAc=3:1) shows the reaction is complete. Add water to the mixture, extract with DCM (10 mL×3), combine the organic layer, wash with 1N HCl solution, brine sequentially, and dry over anhydrous Na2SO4. Concentrate under reduced pressure to get the product (1.50 g, 89%).

Workup

  1. additionAfter addition
  2. extractionAdd water to the mixture, extract with DCM (10 mL×3)
  3. washwash with 1N HCl solution, brine sequentially
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-a125d2997da241b3a8dcada61037e763
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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