Hydrochloric Acid → HCID 13412531, compound

HRID 409709Notes

Reaction equation

HRID 409709 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].Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].Cl>ClCCl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:15])[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15891Phenyl chloroformateHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 13412531HCID 13412531, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At room temperature, 4-chloro-3-trifluoromethyl-aniline (4.9 g, 25 mmol, 1 eq) was dissolved in dichloromethane (50 mL). A solution of phenyl chloroformate (3.9 g, 25 mmol, 1 eq) in dichloromethane (10 mL) was added, and the mixture was stirred for 1 h at room temperature. Dilute hydrochloride (1 N, 50 mL) was added, and the mixture was washed with water (40 mL×3) and separated. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent in the filtrate was removed to give the title compound (7.5 g, purity 99%, yield 94%) as an off-white solid.

Workup

  1. washthe mixture was washed with water (40 mL×3)
  2. customseparated
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent in the filtrate was removed

Sources & evidence

ORD record
ord-a61c48dd2a794f3c8ea09afccdd30c8b
Source dataset
uspto-grants-2014_06
Patent number
US08759531B2

Reaction notes

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