Triethylamine → 3,3-Dimethyl-2-methylcarbamyloximino-1-methylsulfonyloxybutane

HRID 263115Notes

Reaction equation

HRID 263115 reaction equation
[OH:1][C:2](=[N:12][OH:13])[CH:3]([C:8](=[O:11])[NH:9][CH3:10])[C:4]([CH3:7])([CH3:6])[CH3:5].[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:7][C:4]([CH3:5])([CH3:6])[CH:3]([C:8](=[O:11])[NH:9][CH3:10])[C:2](=[N:12][OH:13])[O:1][S:15]([CH3:14])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178485727HCID 178485727, compound

Product 1

HCID 867329273,3-Dimethyl-2-methylcarbamyloximino-1-methylsulfonyloxybutane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 7.5 g (0.04 mol) of 1-hydroxy-3,3-dimethyl-2-methylcarbamyloximinobutane and 5.0 g (0.044 mol) of methanesulfonyl chloride in 50 ml of benzene is treated dropwise with 4.6 g (0.044 mol) of triethylamine with cooling to keep the temperature below 35° C. After the addition, the stirred mixture is heated at 35° C. for two hours and then washed with aqueous sodium bicarbonate and with water. The organic layer is dried over magnesium sulfate, filtered, and stripped of volatiles to give 6.7 g (63%) of amber, viscous liquid residue, nD25 1.4810.

Workup

  1. temperaturewith cooling
  2. customthe temperature below 35° C
  3. additionAfter the addition
  4. washwashed with aqueous sodium bicarbonate and with water
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customto give 6.7 g (63%) of amber, viscous liquid residue

Sources & evidence

ORD record
ord-0399855ea8ea44b8aa5e062958a4ee21
Source dataset
uspto-grants-1979_05
Patent number
US04156082

Reaction notes

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