1-Dodecanol → Dodecyl(chlorosulfonyl)carbamate

HRID 5645

Reaction equation

HRID 5645 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl:14][S:15]([N:18]=[C:19]=[O:20])(=[O:17])=[O:16]>CCOCC>[CH2:1]([O:13][C:19](=[O:20])[NH:18][S:15]([Cl:14])(=[O:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 81931-DodecanolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 10758631Dodecyl(chlorosulfonyl)carbamateYield 101.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of n-dodecyl alcohol (10.7 g, 57.4 mmoles) in 100 mL Et2O was added dropwise to a solution of chlorosulfonyl isocyanate (5.0 mL, 57.4 mmoles) in 100 mL Et2O at ~15° C. under an atmosphere of N2. The resulting mixture was stirred for 2 hours and concentrated in vacuo. The residue was triturated with cold hexanes to give a white solid and collected by filtration to give 19.12 g of a white solid, mp 62°-63° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with cold hexanes
  3. customto give a white solid
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0b945865b6ed43e89b1d0e52682f9023
Source dataset
uspto-grants-1993_09
Patent number
US05245068

Linked notes

Loading…