Sulfuryl chloride → HCID 13020367, compound

HRID 847652Notes

Reaction equation

HRID 847652 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([C:10]1[O:14][N:13]=[C:12]([NH:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>C(Cl)Cl>[C:6]([C:10]1[O:14][N:13]=[C:12]([NH:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[C:11]=1[Cl:4])([CH3:9])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 156446Cyclopropanecarboxamide, N-[5-(1,1-dimethylethyl)-3-isoxazolyl]-

Product 1

HCID 13020367HCID 13020367, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylene chloride (20 ml) and sulfuryl chloride (5.40 g) are added to N-(5-t-butyl-3-isoxazolyl)cyclopropanecarboxamide (4.17 g) and refluxed with heating for 1.5 hours. The methylene chloride and the unreacted sulfuryl chloride are evaporated under reduced pressure. The residue is chromatographed on a column of silica gel and recrystallized from benzene to give N-(5-t-butyl-4-chloro-3-isoxazolyl)cyclopropanecarboxamide (4.10 g) as colorless needles melting at 129.5° to 131.0° C.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 1.5 hours
  3. customThe methylene chloride and the unreacted sulfuryl chloride are evaporated under reduced pressure
  4. customThe residue is chromatographed on a column of silica gel
  5. customrecrystallized from benzene

Sources & evidence

ORD record
ord-504ffcc17ef74223b61a19a1297228a5
Source dataset
uspto-grants-1981_10
Patent number
US04293328

Reaction notes

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