m-Toluidine → HCID 19860393, compound

HRID 1721871Notes

Reaction equation

HRID 1721871 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=1>COC>[NH2:1][C:2]1[N:7]=[C:6]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)[C:5]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 19860394HCID 19860394, compound

Product 1

HCID 19860393HCID 19860393, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 8254Dimethyl EtherSolvent

Procedure

To a suspension of 2-amino-4-chloro-N-(1,1-dimethylethyl)-5-pyrimidinesulfonamide (2.64 g, 10 mmol) in 7 mL dimethylether was added meta-toluidine (2.46 g, 23 mmol) and the reaction stirred at room temperature for 1 hour and then at 60° C. for 1/2 hour. The solvent was removed and the residue taken up in ethyl acetate. The ethyl acetate was washed with water, saline, dried, and the solvent removed in vacuo. The residue was triturated with ether and the crystals collected by suction filtration and dried to give 2.10 g of the identical product obtained in Step 1.

Workup

  1. waitat 60° C. for 1/2 hour
  2. customThe solvent was removed
  3. washThe ethyl acetate was washed with water, saline
  4. customdried
  5. customthe solvent removed in vacuo
  6. customThe residue was triturated with ether
  7. filtrationthe crystals collected by suction filtration
  8. customdried

Sources & evidence

ORD record
ord-baacf6034d2d46acad5193b7fc16f874
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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