Pyridine → Methyl 4-iodo-2-isocyanatosulfonylbenzoate

HRID 2293914Notes

Reaction equation

HRID 2293914 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[S:12]([NH2:15])(=[O:14])=[O:13])=[O:4].S(Cl)(Cl)=O.N1C=CC=CC=1.[C:26](Cl)(Cl)=[O:27]>ClCCCl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[S:12]([N:15]=[C:26]=[O:27])(=[O:14])=[O:13])=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 24386Thionyl ChlorideHCID 109478222-(Aminosulfonyl)-4-iodobenzoic acid methyl ester

Product 1

HCID 11326070Methyl 4-iodo-2-isocyanatosulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

50 g of the sulfonamide obtained in Example 6 are suspended in 150 ml of 1,2-dichloroethane and the suspension is treated with 27.7 ml of thionyl chloride. The mixture is heated at the boil for 4 hours, cooled to 50°-55° C. and treated with 0.5 ml of pyridine, and phosgene is passed for 31/2 hours into the solution which has now been brought to the boil. The mixture is concentrated under reduced pressure with the exclusion of moisture. The crude sulfonyl isocyanate which remains (52.6 g) crystallises upon standing.

Workup

  1. temperatureThe mixture is heated at the boil for 4 hours
  2. temperaturecooled to 50°-55° C.
  3. custom2 hours
  4. concentrationThe mixture is concentrated under reduced pressure with the exclusion of moisture
  5. customcrystallises

Sources & evidence

ORD record
ord-7bf635651a5e4abfb521d1864d8fd480
Source dataset
uspto-grants-1997_11
Patent number
US05688745

Reaction notes

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