Pyridine → HCID 13412531, compound

HRID 2094773Notes

Reaction equation

HRID 2094773 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[Cl:10])[NH2:6].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].CCCCCC>ClCCl>[Cl:10][C:9]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:2]([F:1])([F:11])[F:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8058HexaneHCID 15891Phenyl chloroformateHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 13412531HCID 13412531, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-trifluoromethyl-4-chloroaniline (25 g, 0.1278 mol) and pyridine (26 ml, 0.3195 mol) were dissolved in dichloromethane (250 ml). The reaction mass was cooled to 0° C. to −5° C. and a solution of phenyl chloroformate (22 ml, 0.1661 mol) in dichloromethane (100 ml) was added drop wise maintaining the temperature of the reaction mass below 0° C. The reaction mass was stirred at 0° C. to 5° C. for 1-2 hours and quenched with water (200 ml) below 10° C. The organic phase was separated and washed with water followed by 1N HCl. It was then dried over sodium sulfate and concentrated to obtain solid. This solid was agitated with hexane (350 ml) at ambient temperature for 2-3 hours and filtered. The obtained product was vacuum dried at 50° C. to give phenyl 4-chloro-3-(trifluoromethyl)phenylcarbamate (36 g) as white solid.

Workup

  1. temperatureThe reaction mass was cooled to 0° C. to −5° C.
  2. temperaturewise maintaining the temperature of the reaction mass below 0° C
  3. customquenched with water (200 ml) below 10° C
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialIt was then dried over sodium sulfate
  7. concentrationconcentrated
  8. customto obtain solid
  9. filtrationfiltered
  10. customdried at 50° C.

Sources & evidence

ORD record
ord-e12a0e1fc125493baa1fc4fb18121c96
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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