Butylamine → HCID 4447312, compound

HRID 2372634Notes

Reaction equation

HRID 2372634 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([NH2:10])[CH2:7][CH2:8][CH3:9]>ClCCl.C(Cl)(Cl)Cl>[CH2:6]([NH:10][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 8007ButylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 4447312HCID 4447312, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (6.76 ml., 87.3 mmole, 1.0 eq.) was dissolved in distilled dichloromethane (44 ml., 0.5M). The solution was cooled in an ice bath and treated dropwise with n-butylamine (17.3 ml., 175 mmole, 2.0 eq.). After the addition was complete, the clear solution was stirred overnight at room temperature. The mixture was diluted with chloroform (200 ml.), dried, washed with 0.5N HCl (2×200 ml.) and saturated NaCl solution (200 ml.), dried (MgSO4) and freed of solvent in vacuo leaving an oil. This was purified by distillation to give N-butylmethanesulfonamide (11.4 g., 86%, b.p. 106°-110°/0.5 mm) which solidified on standing.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. additionAfter the addition
  3. customdried
  4. washwashed with 0.5N HCl (2×200 ml.) and saturated NaCl solution (200 ml.)
  5. dry with materialdried (MgSO4)
  6. customleaving an oil
  7. distillationThis was purified by distillation

Sources & evidence

ORD record
ord-e5c0453a4256476bac64ea297fa91375
Source dataset
uspto-grants-1992_03
Patent number
US05098924

Reaction notes

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