Pyridine → HCID 10543884, compound

HRID 1532599Notes

Reaction equation

HRID 1532599 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]([N:15]=[C:16]=S)([CH3:14])[CH3:13].CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1.N1C=CC=CC=1>CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[N:11]=[C:16]([NH:15][CH:12]([CH3:14])[CH3:13])[NH:10][C:4]=2[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 10848635HCID 10848635, compound

Product 1

HCID 10543884HCID 10543884, compoundYield 608.4%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

3-Bromo-4,5dichloro-1,2-phenylenediamine (25.0 g, 97.7 mmol), isopropyl isothiocyanate (11.2 g, 110.5 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (56.8 g, 134.1 mmol) and pyridine (500 mL) were used according to general procedure I. The product was isolated by silica gel chromatography using 7:3 hexane/ethyl acetate to afford 192 g (62%) of a tan solid; m p. 247-249° C. Anal. Calcd for C10H10BrCl2N3-(0.08 C6H14): C, 38.15; H, 3.40; N, 12.74. Found: C, 38.15; H, 3.39; N, 12.77.

Workup

  1. customThe product was isolated by silica gel chromatography

Sources & evidence

ORD record
ord-5d5ae07c0e8d4e8d82ae7dad81999424
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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