Tert-Butylamine → N-tert-butylmethanesulfonamide

HRID 1857587Notes

Reaction equation

HRID 1857587 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH3:6][S:7](Cl)(=[O:9])=[O:8]>C1COCC1>[C:1]([NH:5][S:7]([CH3:6])(=[O:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Conditions

Temperature
0 °C

Procedure

t-Butylamine (105 ml, 1.0 mole) was dissolved in THF (about 950 ml) and cooled to 0° C. Methanesulfonylchloride (57.2 g) was added and the solution allowed to warm to room temperature overnight. The mixture was filtered and the filtrate stripped to dryness. The resulting residue was dissolved in methylene chloride and washed with 1N HCl followed by washing first with water and then with brine (water saturated with NaCl). The methylene chloride layer was dried over Na2SO4, filtered, and stripped to dryness. The resulting residue was dissolved in pentane, and the solid which crystallized was collected and dried.

Workup

  1. temperatureto warm to room temperature overnight
  2. filtrationThe mixture was filtered
  3. dissolutionThe resulting residue was dissolved in methylene chloride
  4. washwashed with 1N HCl
  5. washby washing first with water
  6. dry with materialThe methylene chloride layer was dried over Na2SO4
  7. filtrationfiltered
  8. dissolutionThe resulting residue was dissolved in pentane
  9. customthe solid which crystallized
  10. customwas collected
  11. customdried

Sources & evidence

ORD record
ord-1b5cd7a189954bd4ad89ddf2e5b4dba6
Source dataset
uspto-grants-2000_11
Patent number
US06147115

Reaction notes

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