Chlorobenzene → HCID 23069967, compound

HRID 644467Notes

Reaction equation

HRID 644467 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[NH2:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=2)[N:17]=1.P(Cl)(Cl)Cl.ClC1C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:19]=[C:20]([C:28]([F:29])([F:30])[F:31])[CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=2)[N:17]=1)=[O:9]

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 94475-Chlorosalicylic AcidHCID 24387Phosphorus trichlorideHCID 27257694-[3,5-Bis(trifluoromethyl)phenyl]-1,3-thiazol-2-amine

Product 1

HCID 23069967HCID 23069967, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chlorosalicylic acid (172.6 mg, 1 mmol), 2-amino-4-[3,5-bis(trifluoromethyl)phenyl]thiazole (312.2 mg, 1 mmol), phosphorus trichloride (44 μL, 0.5 mmol) and monochlorobenzene (5 mL) was refluxed for 4 hours. After the reaction mixture was cooled to room temperature, it was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1→2:1) to give the title compound (109.8 mg, 23.5%) as a pale yellow white powder.

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionextracted with ethyl acetate
  3. washAfter the ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1→2:1)

Sources & evidence

ORD record
ord-cf23fa17661a42a3a0b6ed22fdedbd75
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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