p-Toluenesulfonic acid → HCID 22995425, compound

HRID 1167084Notes

Reaction equation

HRID 1167084 reaction equation
[Br:1][C:2]1[C:3]([NH2:11])=[C:4]([NH2:10])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].[CH:12]1([N:15]=[C:16]=S)[CH2:14][CH2:13]1.O1CCN(CCN=C=N)CC1.CC1C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1>[Br:1][C:2]1[C:3]2[N:11]=[C:16]([NH:15][CH:12]3[CH2:14][CH2:13]3)[NH:10][C:4]=2[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 92463Cyclopropyl isothiocyanateHCID 10848635HCID 10848635, compoundHCID 20387999HCID 20387999, compound

Product 1

HCID 22995425HCID 22995425, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Bromo-4,5-dichloro-1,2-phenylenediamine (5.12 g, 20.0 mmol), cyclopropyl isothiocyanate (2.18 g, 21.98 mmol), 1-cyclohexyl-3-(2-morpholinoethylcarbodiimide metho-p-toluenesulfonate (11.0 g, 25.97 mmol) and pyridine (75 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 2.23 g (53%) of a white solid. MS (CI): m/z 319 amu. Anal. Calcd for C10H8BrCl2N3(0.35 C4H8O2): C, 38.92; H, 3.09; N, 11.94. Found: C, 39.17; H, 3.05; N, 11.94.

Workup

  1. customThe product was recrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-e45ef64bfde24032b3f1288fee55b4dd
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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