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

HRID 2232022Notes

Reaction equation

HRID 2232022 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 an sun lamp. After 8 hours and 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 an 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-249023a74fa84417a1604ddd6a4a9b6c
Source dataset
uspto-grants-1988_11
Patent number
US04786314

Reaction notes

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