Acetic Anhydride → HCID 178527357, compound

HRID 1988902Notes

Reaction equation

HRID 1988902 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:6]([NH2:8])[CH:7]=1.C([O-])(=O)C.[K+].C(OC(=O)C)(=O)C.C1OCCOCCOCCOCCOCCOC1.C(O[N:55]=O)(C)(C)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:9]([S:10]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)(=[O:11])=[O:12])=[N:55][NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 10906Tert-Butyl nitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 586565135-Bromo-2-[(4-fluorobenzene-1-sulfonyl)methyl]aniline2×

Product 1

HCID 178527357HCID 178527357, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of (5-bromo-2-{[(4-fluorophenyl)sulfonyl]methyl}phenyl)amine (Intermediate 68) (0.42 g) in chloroform (10 ml) was added potassium acetate (0.135 g) and acetic anhydride (0.24 ml). The mixture was heated under nitrogen at reflux for 18 h. 18-Crown-6 (0.64 g) and tert-butylnitrite (0.435 ml) were added and the mixture was stirred at reflux for a further 42 h. The mixture was concentrated under vacuum and the residue was purified by column chromatography on silica eluting with cyclohexane:ethylacetate (4:1) to give the title compound (0.16 g).

Workup

  1. temperatureThe mixture was heated under nitrogen
  2. temperatureat reflux for 18 h
  3. temperatureat reflux for a further 42 h
  4. concentrationThe mixture was concentrated under vacuum
  5. customthe residue was purified by column chromatography on silica eluting with cyclohexane:ethylacetate (4:1)

Sources & evidence

ORD record
ord-5ec11b7628b4469aa5e6f7f5dca8e6d8
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

Loading…