Pyridine → Methyl 4-iodo-2-isocyanatosulfonylbenzoate

HRID 2211276Notes

Reaction equation

HRID 2211276 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-80d61e12408245a39394dc76ebcc6dc1
Source dataset
uspto-grants-1995_10
Patent number
US05463081

Reaction notes

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