Triethylamine → HCID 13799777, compound

HRID 1906382Notes

Reaction equation

HRID 1906382 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[N:4].C(N(CC)CC)C.[CH3:14][O:15][CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:5][C:2]([NH:1][S:18]([CH2:17][CH2:16][O:15][CH3:14])(=[O:20])=[O:19])([CH3:6])[C:3]#[N:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 880222-Amino-2-methylpropionitrileHCID 134802212-Methoxyethane-1-sulfonyl chloride2×

Product 1

HCID 13799777HCID 13799777, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 10 g (0.12 mole) 2-amino-2-methyl-propionitrile and 12.1 g (0.12 mole) triethylamine in about 200 ml methylene chloride cooled by an ice bath, 18.8 g (0.12 moles) 2-methoxyethane sulfonyl chloride (the product of Example 19) in 15 ml methylene chloride were added dropwise. The reaction mixture was then stirred at room temperature over the weekend. The reaction mixture was washed three times with equal amounts (about 200 ml) water, dried over magnesium sulfate, filtered and stripped to give an oil. The oil was recrystallized from ethyl ether/petroleum ether to give 15.0 g of the above-identified product, melting point 58°-60° C.

Workup

  1. temperaturecooled by an ice bath
  2. washThe reaction mixture was washed three times with equal amounts (about 200 ml) water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customto give an oil
  6. customThe oil was recrystallized from ethyl ether/petroleum ether

Sources & evidence

ORD record
ord-2965d0e7164f41b3bdeb8cfb7e0d9f60
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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