Ammonia → 4-[(Methylsulfonyl)amino]butanamide

HRID 2073346Notes

Reaction equation

HRID 2073346 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([NH:9]CCN)(=[O:8])[CH3:7].[CH2:13]([N:15](CC)CC)[CH3:14].N>C(Cl)Cl>[CH3:1][S:2]([NH:15][CH2:13][CH2:14][CH2:7][C:6]([NH2:9])=[O:8])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66082N-(2-aminoethyl)acetamide

Product 1

HCID 222467414-[(Methylsulfonyl)amino]butanamideYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.86 grams (104 mmol) of methanesulfonyl chloride was added to a solution of 10.2 grams (100 mmol) of acetylethylenediamine and 10.5 grams (104 mmol) of triethylamine in cold (0° C.) methylene chloride and the mixture was stirred for 3 hours. At the end of this period, the mixture was concentrated to obtain a residue. To the residue was added 500 milliliters of ammonia saturated chloroform, the resulting mixture was filtered to removed undesired by-product and the filtrate was concentrated to obtain 14.5 grams (80 percent yield) of 2-methanesulfonylaminoethylacetamide.

Workup

  1. concentrationAt the end of this period, the mixture was concentrated
  2. customto obtain a residue
  3. filtrationthe resulting mixture was filtered
  4. customto removed
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-100d242803044b8cb05778ab6d8e481e
Source dataset
uspto-grants-1990_04
Patent number
US04916223

Reaction notes

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