p-Toluenesulfonyl isocyanate → HCID 18676534, compound

HRID 1635708Notes

Reaction equation

HRID 1635708 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([CH3:29])[C:21]=1[S:22]([CH2:25][N+:26]([O-:28])=[O:27])(=[O:24])=[O:23])[NH2:18]>C(Cl)Cl>[CH3:29][C:20]1[CH:19]=[C:17]([NH:18][C:11]([NH:10][S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=2)(=[O:8])=[O:9])=[O:12])[CH:16]=[C:15]([CH3:14])[C:21]=1[S:22]([CH2:25][N+:26]([O-:28])=[O:27])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 195716Ici 222155

Product 1

HCID 18676534HCID 18676534, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.55 ml (10.2 mmol) of p-toluenesulphonyl isocyanate in 15.5 ml of anhydrous methylene chloride is added dropwise to a suspension, maintained under a nitrogen atmosphere, of 2.6 g (10.6 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline in 52 ml of anhydrous methylene chloride. The temperature of the reaction medium rises spontaneously by 2° C. Stirring of the solution obtained is continued for 30 minutes at room temperature. The reaction medium is then concentrated to dryness under reduced pressure; the residue is purified by chromatography on a column of silica (eluent: methylene chloride and then a 9/1 methylene chloride/methanol mixture) and crystallization from methylene chloride, to give 2.5 g (57%) of 1-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]-3-[(4-methylphenyl)sulphonyl]urea.

Workup

  1. customrises spontaneously by 2° C
  2. customobtained
  3. concentrationThe reaction medium is then concentrated to dryness under reduced pressure
  4. customthe residue is purified by chromatography on a column of silica (eluent
  5. custommethylene chloride and then a 9/1 methylene chloride/methanol mixture) and crystallization from methylene chloride

Sources & evidence

ORD record
ord-71153b2b848a449393bf09ca2449d26e
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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