N-bromobutanimide → 5-Bromomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

HRID 477721Notes

Reaction equation

HRID 477721 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])(=[O:8])=[O:7])([CH3:4])[CH3:3].C1C(=O)N([Br:25])C(=O)C1>C(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:25][CH2:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH3:17])=[C:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:8])=[O:7])[CH:14]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 934523N-tert-butyl-2-methoxy-5-methylbenzenesulfonamide

Product 1

HCID 139214535-Bromomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamideYield 96.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 27 g of N-(1,1-dimethylethyl)-2-methoxy-5-methylbenzenesulfonamide (E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 603), 19.6 g NBS and 0.3 g azobisisobutyronitrile in 200 ml CH2Cl2 was refluxed and illuminated with a sun lamp. After 8 hours the lamp was turned off and the reaction was refluxed for another 24 hr. The reaction was allowed to cool. The reaction mixture was washed with 200 ml of a 1:1:1:1 mixture of brine:sodium sulfite-sodium bicarbonate-water. The organic layer was dried (MgSO4), treated with charcoal and filtered through a 5 g plug of silica gel. The plug was washed with 100 ml of chloroform. The combined organic fractions were evaporated to give 34 g of solid, m.p. 137°-142° C.;

Workup

  1. temperaturewas refluxed
  2. customilluminated with a sun lamp
  3. temperaturethe reaction was refluxed for another 24 hr
  4. temperatureto cool
  5. washThe reaction mixture was washed with 200 ml of a 1:1:1:1 mixture of brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. additiontreated with charcoal
  8. filtrationfiltered through a 5 g plug of silica gel
  9. washThe plug was washed with 100 ml of chloroform
  10. customThe combined organic fractions were evaporated

Sources & evidence

ORD record
ord-7ae06c0bd9dc4efaaa44ddd02f38c2d4
Source dataset
uspto-grants-1989_12
Patent number
US04889550

Reaction notes

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