Thionyl Chloride → HCID 60142727, compound

HRID 1805272Notes

Reaction equation

HRID 1805272 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14](O)=[O:15])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[C:21]=2[C:22]([F:25])([F:24])[F:23])[O:11][N:10]=1.S(Cl)(Cl)=O.[CH3:36][S-:37].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14](=[O:15])[S:37][CH3:36])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[C:21]=2[C:22]([F:25])([F:24])[F:23])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 4378561Sodium methanethiolateHCID 68153033HCID 68153033, compound

Product 1

HCID 60142727HCID 60142727, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylic acid (30 mg, 0.066 mmol) was treated with thionylchloride (1.5 mL) and stirred at reflux for 2 h. The mixture was concentrated under reduced pressure. The intermediate was treated with benzene (3×) and the benzene was evaporated to remove water. Then, the obtained mixture was dissolved in benzene (1.5 mL) and sodium methanethiolate (32.5 mg, 0.46 mmol) was added. The reaction mixture was stirred at reflux for 5 h. The mixture was diluted with dichloromethane and washed with water (3×), dried over sodium sulfate, filtered and concentrated under reduced pressure. The product (example IB-68) was purified by pTLC (1:1 EE/PE) to give 3 mg of a white solid (yield 9%). Result of LC/MS MH+: 482.76; 1H NMR (CDCl3): 2.33 (t, 3H), 7.19 (t, 1H), 7.33-7.55 (m, 6H), 8.23 (s, 1H)

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionThe intermediate was treated with benzene (3×)
  4. customthe benzene was evaporated
  5. customto remove water
  6. dissolutionThen, the obtained mixture was dissolved in benzene (1.5 mL)
  7. stirringThe reaction mixture was stirred
  8. temperatureat reflux for 5 h
  9. washwashed with water (3×)
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0fa68f42e04e4704bf7de3a418cfb913
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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