Triethylamine → 1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

HRID 440703Notes

Reaction equation

HRID 440703 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].[OH:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>C(OCC)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([O:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 3592851,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamateYield 69.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 25.0 grams (0.114 mole) of 2,4,6-trimethylbenzenesulfonyl chloride and 15.3 grams (0.114 mole) of 1,1-dimethylethyl N-hydroxycarbamate in 350 mL of diethyl ether was cooled in an ice-water bath, and 11.4 grams (0.114 mole) of triethylamine was added dropwise. Upon completion of the addition, the reaction mixture was allowed to warm to ambient temperature as it stirred for about 18 hours. The reaction mixture was then filtered, and the filtrate was concentrated under reduced pressure to a residue, which was slurried with toluene and petroleum ether. The resultant solid was collected by filtration, yielding 25.0 grams of 1,1-dimethylethyl N-(2,4,6-trimethylphenylsulfonyloxy)carbamate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure to a residue, which
  4. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-eacf51e1a654425e8eb05774c51177d5
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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