Thionyl Chloride → 4-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

HRID 646000Notes

Reaction equation

HRID 646000 reaction equation
S(Cl)([Cl:3])=O.N1C2C=CC=CC=2N=N1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[C:22]1[C:26]([CH2:27]O)=[C:25]([CH:29]([CH3:31])[CH3:30])[O:24][N:23]=1>ClCCl>[Cl:3][CH2:27][C:26]1[C:22]([C:16]2[C:15]([Cl:14])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:21])=[N:23][O:24][C:25]=1[CH:29]([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanolHCID 178418385HCID 178418385, compound

Product 1

HCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazoleYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (87 mL, 1.20 mol) was added dropwise to a stirred solution of benzotriazole (143 g, 1.20 mol) in dichloromethane (400 mL) at room temperature. The resulting solution was added dropwise during 30 min to a stirred solution of [3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methanol (263 g, 0.92 mol) in dichloromethane (700 mL). A very mild exothermic reaction occurred with precipitation of benzotriazole hydrochloride. The mixture was filtered to remove the benzotriazole hydrochloride. The filtrate was washed with water (2×800 mL), 1N sodium hydroxide (800 mL) and then dried over anhydrous sodium sulfate. The resulting solution was filtered and concentrated to give 288 g of the product as a pale yellow oil. 1H NMR (DMSO-d6): δ 7.66 (m, 2H), 7.61-7.57 (m, 1H), 4.47 (s, 2H), 3.45 (septet, J=7 Hz, 1H), 1.31 (d, J=7 Hz, 6H). ESI-LCMS m/z 279 (M+H)+.

Workup

  1. customA very mild exothermic reaction
  2. customoccurred with precipitation of benzotriazole hydrochloride
  3. filtrationThe mixture was filtered
  4. customto remove the benzotriazole hydrochloride
  5. washThe filtrate was washed with water (2×800 mL), 1N sodium hydroxide (800 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe resulting solution was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-49bf97a035d54171afb36686dce47077
Source dataset
uspto-grants-2010_04
Patent number
US07705028B2

Reaction notes

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