2-Ethoxyphenol → 2-Ethoxyphenoxysulfonyl isocyanate

HRID 1030006Notes

Reaction equation

HRID 1030006 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[CH3:9]>C1(C)C(C)=CC=CC=1>[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3])[CH3:9]

Participants

4

Reactant 2

HCID 667552-EthoxyphenolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 190299582-Ethoxyphenoxysulfonyl isocyanate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

67.9 g (0.48 mol) of chlorosulfonyl isocyanate are added dropwise at 25° C. to a solution of 55.2 g (0.4 mol) of 2-ethoxyphenol in 500 ml of xylene. When the dropwise addition is complete, the temperature is increased slowly to 140° C. and the mixture is refluxed for 2.5 hours. The mixture is cooled, and the solvent as well as excess chlorosulfonyl isocyanate are removed on a rotary evaporator. The yellow oil which remains (97.2 g=100% of theory) is employed without further purification.

Workup

  1. additionWhen the dropwise addition
  2. temperaturethe mixture is refluxed for 2.5 hours
  3. temperatureThe mixture is cooled
  4. customthe solvent as well as excess chlorosulfonyl isocyanate are removed on a rotary evaporator
  5. customis employed without further purification

Sources & evidence

ORD record
ord-aec70c62939d41d5a380f35e73bc23fc
Source dataset
uspto-grants-1992_04
Patent number
US05104443

Reaction notes

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