Acetic Anhydride → HCID 19608684, compound

HRID 1781450Notes

Reaction equation

HRID 1781450 reaction equation
ClC1C=C(C(=NO)CC2C=CC(SC)=CC=2)C=CC=1OC.C(OC(=O)C)(=O)C.[Cl:29][C:30]1[CH:31]=[C:32]([C:38]2[C:42]([C:43]3[CH:48]=[CH:47][C:46]([S:49]([CH3:52])(=O)=O)=[CH:45][CH:44]=3)=[C:41]([CH3:53])[O:40][N:39]=2)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].OOS([O-])=O.[K+]>>[Cl:29][C:30]1[CH:31]=[C:32]([C:38]2[C:42]([C:43]3[CH:48]=[CH:47][C:46]([S:49][CH3:52])=[CH:45][CH:44]=3)=[C:41]([CH3:53])[O:40][N:39]=2)[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 19608716HCID 19608716, compoundHCID 23707502Potassium hydroxy sulfiteHCID 73630007HCID 73630007, compound

Product 1

HCID 19608684HCID 19608684, compoundYield 26%

Procedure

3-(3-Chloro-4-methoxyphenyl)-5-methyl-4-[4-(methylthio)phenyl]isoxazole was prepared in 26% yield from 1-(3-chloro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]-ethan-1-one oxime from Step 5 and acetic anhydride by the method described in Example 4, Step 1 and then oxidized to 3-(3-chloro-4 methoxyphenyl)-5-methyl-4-[4-methylsulfonylphenyl]isoxazole with Oxone® by the method described in Example 5, Step 4: Mass spectrum: MLi+=384. High resolution mass spectrum Calc'd. For C18H16ClNO4S: 378.0567. Found: 378.0573.

Sources & evidence

ORD record
ord-685ec2226bcb42d28fd7ce5dc2b140b9
Source dataset
uspto-grants-1997_05
Patent number
US05633272

Reaction notes

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