m-Toluidine → HCID 19860402, compound

HRID 2072789Notes

Reaction equation

HRID 2072789 reaction equation
Cl[C:2]1[C:7]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:6][N:5]=[C:4]([S:16][CH3:17])[N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1>C(Cl)(Cl)Cl>[CH3:13][C:12]([NH:11][S:8]([C:7]1[C:2]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)=[N:3][C:4]([S:16][CH3:17])=[N:5][CH:6]=1)(=[O:10])=[O:9])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 19860404HCID 19860404, compound

Product 1

HCID 19860402HCID 19860402, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Chloro-N-(1,1-dimethylethyl)-2-(methylthio)-5-pyrimidinesulfonamide (1.45 g, 4.91 mmol) was dissolved in chloroform (15 mL). m-Toluidine (1.08 mL, 10.07 mmol, 2.05x) was added, and the mixture was refluxed for 90 minutes. The reaction was cooled to ambient temperature, the chloroform removed under reduced pressure, and the residue crystallized from ethanol and water to yield 1.74 g (4.75 mmoles, 97%) of pale yellow needles, m.p. 177.5°-178° C.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customthe chloroform removed under reduced pressure
  3. customthe residue crystallized from ethanol and water

Sources & evidence

ORD record
ord-b59f25d70d744f5e8e0bb01753798678
Source dataset
uspto-grants-1990_04
Patent number
US04914203

Reaction notes

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