Benzenesulfonyl chloride → HCID 20294478, compound

HRID 1390044Notes

Reaction equation

HRID 1390044 reaction equation
[Cl:1][C:2]1[C:3]([OH:8])=[N:4][O:5][C:6]=1[CH3:7].[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:19]N1C(=O)CCC1=O>C(N(CC)CC)C>[C:9]1([S:15]([O:8][C:3]2[C:2]([Cl:1])=[C:6]([CH2:7][Br:19])[O:5][N:4]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 67184N-bromobutanimideHCID 178435011HCID 178435011, compound

Product 1

HCID 20294478HCID 20294478, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Chloro-3-hydroxy-5-methylisoxazole was reacted with benzenesulphonyl chloride in the presence of triethylamine to give 3-benzenesulphonyloxy-4-chloro-5-methylisoxasole, which was then reacted with N-bromosuccinimide to give 3-benzenesulphonyloxy-5-bromomethyl-4-chloroisoxazole. This was then treated by the procedure described in Preparation 10, to afford benzhydryl 4-chloro-3-hydroxyisoxazol-5-ylmethylthioacetate.

Workup

  1. customto give 3-benzenesulphonyloxy-4-chloro-5-methylisoxasole, which

Sources & evidence

ORD record
ord-0ec0de7f4028414d80f92eabb97fb82f
Source dataset
uspto-grants-1981_01
Patent number
US04247548

Reaction notes

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