4-Toluenesulfonyl chloride → HCID 20324082, compound

HRID 839264Notes

Reaction equation

HRID 839264 reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.O1CCOCC1.C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([O:1][NH:2][C:3](=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 164691Carbamic acid, hydroxy-, butyl ester

Product 1

HCID 20324082HCID 20324082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

26.6 Parts of butyl N-hydroxycarbamate and 38.1 parts of p-toluenesulphonylchloride are stirred in 100 parts of dioxan maintained at 0° to 5° C. 20.4 Parts of triethylamine are added during 1 hour keeping the pH at 3 to 6. The mixture is then stirred for 18 hours at 25° C and added to 500 parts of water. The oily precipitate is taken up into 200 parts toluene, and the solution is dried, filtered and evaporated to constant weight at 40° C under reduced pressure to give 52 parts of butyl N-p-toluenesulphonyloxycarbamate as a yellow oil.

Workup

  1. temperaturemaintained at 0° to 5° C
  2. customthe solution is dried
  3. filtrationfiltered
  4. customevaporated to constant weight at 40° C under reduced pressure

Sources & evidence

ORD record
ord-e67c88ef87754f8e9b14457a593cc032
Source dataset
uspto-grants-1978_06
Patent number
US04094863

Reaction notes

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