Benzenesulfonyl chloride → Nonyl [(benzenesulfonyl)oxy]carbamate

HRID 839261Notes

Reaction equation

HRID 839261 reaction equation
C(N(CC)CC)C.[CH2:8]([O:17][C:18](=[O:21])[NH:19][OH:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O1CCOCC1.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[CH2:8]([O:17][C:18](=[O:21])[NH:19][O:20][S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:36])=[O:35])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 21314104Nonyl hydroxycarbamate

Product 1

HCID 54340962Nonyl [(benzenesulfonyl)oxy]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

20.4 Parts of triethylamine are added to a stirred mixture of 40.6 parts of nonyl-N-hydroxycarbamate, 100 parts of dioxan and 35.3 parts of benzene sulphonyl chloride at 0° C keeping the pH in the range 2 to 5. The mixture is stirred for 18 hours at 25° C then added to 500 parts of water. The oily product is separated into 300 parts of toluene and the solution is washed with water, dried and evaporated at 40° l C under reduced pressure to give 72 parts of nonyl-N-benzenesulphonyloxycarbamate as a colourless oil.

Workup

  1. customThe oily product is separated into 300 parts of toluene
  2. washthe solution is washed with water
  3. customdried
  4. customevaporated at 40° l C under reduced pressure

Sources & evidence

ORD record
ord-270a5b0e176441af9e5ceeab05d5c476
Source dataset
uspto-grants-1978_06
Patent number
US04094863

Reaction notes

Loading…