Triethylamine → HCID 13799781, compound

HRID 1906393Notes

Reaction equation

HRID 1906393 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][S:7](Cl)(=[O:9])=[O:8])(=[O:4])=[O:3].[NH2:11][C:12]([CH3:16])([CH3:15])[C:13]#[N:14].C(N(CC)CC)C>O1CCCC1>[C:13]([C:12]([NH:11][S:7]([CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:9])=[O:8])([CH3:16])[CH3:15])#[N:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 880222-Amino-2-methylpropionitrileHCID 1254146071350-98-6

Product 1

HCID 13799781HCID 13799781, compoundYield 133.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5.00 g (24.2 mmoles) 2-(methylsulfonyl)ethylsulfonyl chloride (Example 32) in 50 ml dry tetrahydrofuran, a solution of 2.11 g (0.025 moles) 2-amino-2-methyl-propionitrile and 2.5 g (0.025 moles) triethylamine in 20 ml dry tetrahydrofuran were added dropwise over 13 minutes. During the course of the addition, the temperature of the mixture rose from 19° C. to 38° C. and a white precipitate formed. After the mixture cooled to room temperature, it was filtered. The solid, inorganic salts, was washed with tetrahydrofuran and ethyl ether. The filtrate and washings were stripped using a rotovap to give 8.2 g of a sticky white solid. Recrystallization of the solid from boiling ethanol gave 3.94 g of the above-identified product, melting point 151°-153° C.

Workup

  1. additionDuring the course of the addition
  2. customrose from 19° C. to 38° C.
  3. customa white precipitate formed
  4. filtrationit was filtered
  5. washThe solid, inorganic salts, was washed with tetrahydrofuran and ethyl ether

Sources & evidence

ORD record
ord-6dee50684de44b7e84ad6d3dbed63016
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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