Chlorosulfonyl isocyanate → HCID 14722020, compound

HRID 326974Notes

Reaction equation

HRID 326974 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH3:8][O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:11]=1[OH:20]>C1(C)C(C)=CC=CC=1>[CH3:16][O:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][CH:19]=[C:10]([O:9][CH3:8])[C:11]=1[O:20][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 80651Methyl 3-methoxysalicylate

Product 1

HCID 14722020HCID 14722020, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

3.4 g (0.024 mol) of chlorosulfonyl isocyanate are added dropwise to a solution of 3.6 g (0.02 mol) of methyl 3-methoxy-salicylate in 20 ml of xylene at 25° C. When the dropwise addition has ended, the temperature is slowly increased to 140° C. and the mixture is heated under reflux for 2.5 hours. It is cooled and the solvent and excess chlorosulfonyl isocyanate are removed on a rotary evaporator. The yellow oil which remains (5.4 g=1004 of theory) is used without further purification.

Workup

  1. additionWhen the dropwise addition
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 2.5 hours
  4. temperatureIt is cooled
  5. customthe solvent and excess chlorosulfonyl isocyanate are removed on a rotary evaporator
  6. customis used without further purification

Sources & evidence

ORD record
ord-acdd9fd9f7d44198b26daaec0a1a2fd4
Source dataset
uspto-grants-1993_12
Patent number
US05272129

Reaction notes

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