Thionyl Chloride → HCID 67171805, compound

HRID 1506463Notes

Reaction equation

HRID 1506463 reaction equation
[CH:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3(O)[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][CH:13]34)=[CH:21][C:20]([CH:25]=[CH2:26])=[CH:19][CH:18]=5)[C:8]=2[C:28]([F:31])([F:30])[F:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1.N1C=CC=CC=1.Cl>[CH:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]=[CH2:26])=[CH:19][CH:18]=5)[C:8]=2[C:28]([F:29])([F:30])[F:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 67170303HCID 67170303, compound

Product 1

HCID 67171805HCID 67171805, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A stirred mixture of 3-(5-cyclohexyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-3,3a,4,5-tetrahydronaphtho[1,2-c]isoxazol-3-ol and thionyl chloride (0.030 g, 0.252 mmol) in toluene (5.0 mL) and pyridine (1.5 mL) was heated at 110° C. for 10 minutes. The reaction mixture was cooled, diluted with 1 N aqueous hydrochloric acid (5.0 mL), and extracted with ethyl acetate (3×20 mL). The ethyl acetate extracts were combined and concentrated to give 3-(5-cyclohexyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole [0.016 g, 0.039 mmol, 16%] as an orange solid. The product had an HPLC ret. time=4.916 min. (condition B). LC/MS M+1=415.08.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-981623af68514454b18f114c82e0a00d
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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