Triethylamine → Methanesulfonamide, N-(1-cyano-1-methylethyl)-

HRID 1906373Notes

Reaction equation

HRID 1906373 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[N:4].C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:5][C:2]([NH:1][S:15]([CH3:14])(=[O:17])=[O:16])([CH3:6])[C:3]#[N:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 880222-Amino-2-methylpropionitrile2×

Product 1

HCID 10855788Methanesulfonamide, N-(1-cyano-1-methylethyl)-Yield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 8.4 g (0.1 mole) 2-amino-2-methylpropionitrile (the product of Example 1), and 10.1 g (0.1 mole) triethylamine in 125 ml methylene chloride, 11.5 g (0.1 mole) methanesulfonyl chloride in 25 ml methylene chloride were added dropwise over about 20 minutes in an exothermic addition reaction. The reaction mixture was stirred 15 minutes, then washed once with 100 ml water, washed twice with 50 ml water, dried over magnesium sulfate, and stripped to give 8.9 g of a brown oil.

Workup

  1. additionwere added dropwise over about 20 minutes in an exothermic addition reaction
  2. washwashed once with 100 ml water
  3. washwashed twice with 50 ml water
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-fb29df81730041f88f1e009e792593bd
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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