Triethylamine → N-{2-[(Dimethylsulfamoyl)amino]ethyl}acetamide

HRID 1193535Notes

Reaction equation

HRID 1193535 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[C:8]([NH:11][CH2:12][CH2:13][NH2:14])(=[O:10])[CH3:9].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][N:2]([CH3:7])[S:3]([NH:14][CH2:13][CH2:12][NH:11][C:8](=[O:10])[CH3:9])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66082N-(2-aminoethyl)acetamideHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 14010264N-{2-[(Dimethylsulfamoyl)amino]ethyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14.3 g (0.1 mole) of dimethylsulfamoyl chloride in 50 ml of methylene chloride was added dropwise to a rapidly stirred solution of 10.2 g (0.1 mole) of acetylethylene diamine and 10.1 g (0.1 mole) of triethylamine in 150 ml of methylene chloride at 25° C. After the addition was completed, the solution was stirred for 30 min and then washed in a separatory funnel with two 100 ml portions of water. The organic phase was separated, and dried over MgSO4, and then concentrated under reduced pressure to afford N-[2[(dimethylamino)sulfonylamino]ethyl]acetamide as an oil. The N-acetyl group was then removed by treatment of the oil with 100 ml of 15% HCl at 80° C. for 6 h. The solution was concentrated under reduced pressure to provide 12.6 g (73%) of product as an oil. The NMR spectrum was consistent with the assigned structure.

Workup

  1. additionAfter the addition
  2. washwashed in a separatory funnel with two 100 ml portions of water
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2bf20a2022294a14a1bc2a70514711f5
Source dataset
uspto-grants-1989_03
Patent number
US04810717

Reaction notes

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