p-Toluenesulfonyl isocyanate → HCID 178427618, compound

HRID 1596616Notes

Reaction equation

HRID 1596616 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:11][C@H:10]([NH:12][OH:13])[CH2:9]2)=[CH:4][CH:3]=1.[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:11][C@H:10]([N:12]([OH:13])[C:24]([NH:23][S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:26])=[CH:15][CH:16]=3)(=[O:22])=[O:21])=[O:25])[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 178526348HCID 178526348, compound

Product 1

HCID 178427618HCID 178427618, compoundYield 148%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of cis-3-(4-fluorophenyl)cyclobutylhydroxylamine (0.9 g, 3 mmol) in THF (20 ml) was added p-toluenesulfonyl isocyanate (1.085 g, 5.5 mmol) at room temperature. The resultant precipitates were collected by filtration and recrystallized from ethyl acetate/EtOH to provide 1.68 g (89% yield) of the title compound as a colorless solid, m.p. 177-178° C. (dec.).

Workup

  1. customThe resultant precipitates
  2. filtrationwere collected by filtration
  3. customrecrystallized from ethyl acetate/EtOH

Sources & evidence

ORD record
ord-ab7b6ccb81774c538db0f93811ea38ae
Source dataset
uspto-grants-2001_09
Patent number
US06291520B1

Reaction notes

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