Thionyl Chloride → HCID 23652403, compound

HRID 644757Notes

Reaction equation

HRID 644757 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.S(Cl)([Cl:24])=O>O1CCOCC1>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([Cl:24])=[O:16])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 133462254-[4-(Trifluoromethyl)benzoyl]benzoic acid

Product 1

HCID 23652403HCID 23652403, compoundYield 134.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-{[4-(Trifluoromethyl)phenyl]carbonyl}benzoic acid (200 mg, 0.68 mmol) was stirred in dioxane (5 mL) and thionyl chloride (0.496 mL, 6.8 mmol) added. The reaction mixture was heated at reflux for 1 h. Further thionyl chloride (0.496 mL, 6.8 mmol) was added and heating continued for 3 h. On cooling, the reaction mixture was concentrated in vacuo to give 4-{[4-(trifluoromethyl)phenyl]carbonyl}benzoyl chloride as an oily white liquid (0.286 g) which was used directly in step 2. Step 2: The acid chloride from step 1 was taken up in DCM (2 mL) and added drop-wise to a mixture of 1,1-dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate (D3) (0.170 g, 0.53 mmol) and triethylamine (0.11 mL) in DCM (2 mL). The reaction mixture was stirred at room temperature under argon overnight then diluted with water (20 mL) and DCM (20 mL). The aqueous layer was extracted with DCM (20 mL) and the combined organic layers were dried, concentrated and purified by column chromatography. Elution with 0-30% EtOAc/pentane gave the title compound as a colourless oil (0.244 g). MS (ES): MH+ 596.2. Description 124

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureheating
  4. temperatureOn cooling
  5. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-78149fe24ec34033956ea7949ff3d168
Source dataset
uspto-grants-2010_04
Patent number
US07700599B2

Reaction notes

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