Thionyl Chloride → HCID 53371510, compound

HRID 405703Notes

Reaction equation

HRID 405703 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]([CH3:14])[C:11]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21]O)=[C:17]([CH3:23])[CH:16]=3)=[CH:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(Cl)([Cl:30])=O>ClCCl.CN(C)C=O>[Cl:30][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2[N:12]([CH3:14])[O:13][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:24]([F:27])([F:26])[F:25])[CH:10]=2)=[CH:16][C:17]=1[CH3:23]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 53371509{4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-methanol

Product 1

HCID 53371510HCID 53371510, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

690 mg of {4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-methanol was dissolved in 20 ml dichloromethane and one drop of N,N-dimethylformamide was then added. Thionylchloride (216 mg) was then added very slowly at room temperature. The mixture turned slight yellow before the end of the addition. The mixture was stirred for 3 hours at ambient temperature and then evaporated to dryness. The residue was dissolved in diethylether, washed with aqueous sodium bicarbonate, then with water and finally dried over anhydrous sodium sulfate. The organic phase was then evaporated to dryness affording 3-(4-chloromethyl-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazole as a resinous product (99% yield), which was used immediately for the further step without purification. 1H-NMR (CDCl3, δ in ppm): 7.29-7.44 (m, 6H), 5.36 (s, 1H), 4.60 (s, 2H), 2.99 (s, 3H), 2.44 (s, 3H).

Workup

  1. additionThe mixture turned slight yellow before the end of the addition
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in diethylether
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialwith water and finally dried over anhydrous sodium sulfate
  6. customThe organic phase was then evaporated to dryness

Sources & evidence

ORD record
ord-6c15daf5e09a4c3692d516aa90eab6a3
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Reaction notes

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