Acetic Anhydride → HCID 178504855, compound

HRID 1988907Notes

Reaction equation

HRID 1988907 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][S:10]([CH3:13])(=[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:49]=O)(C)(C)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:9]([S:10]([CH3:13])(=[O:12])=[O:11])=[N:49][NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 10906Tert-Butyl nitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 58656521Benzenamine, 5-bromo-2-[(methylsulfonyl)methyl]-2×

Product 1

HCID 178504855HCID 178504855, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of {5-bromo-2-[(methylsulfonyl)methyl]phenyl}amine (Intermediate 74) (0.26 g) in chloroform (8 ml) was added potassium acetate (0.11 g) and acetic anhydride (0.195 ml). The mixture was heated under nitrogen at reflux for 18 h. 18-Crown-6 (0.26 g) and tert-butylnitrite (0.35 ml) were added and the mixture was stirred at reflux for a further 88 h. The mixture was concentrated under vacuum and the residue was purified by column chromatography on silica eluting with cyclohexane:ethylacetate (4:1 to 1:1) to give the title compound (0.14 g).

Workup

  1. temperatureThe mixture was heated under nitrogen
  2. temperatureat reflux for 18 h
  3. temperatureat reflux for a further 88 h
  4. concentrationThe mixture was concentrated under vacuum
  5. customthe residue was purified by column chromatography on silica eluting with cyclohexane:ethylacetate (4:1 to 1:1)

Sources & evidence

ORD record
ord-55d4cb9bc9f44940a3fa6a3fa7f3e0d3
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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