1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → HCID 18472118, compound

HRID 2227187Notes

Reaction equation

HRID 2227187 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([F:10])[C:5]([NH2:9])=[C:6]([NH2:8])[CH:7]=1.[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>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([F:10])[C:5]2[N:9]=[C:16]([NH:15][CH:12]([CH3:14])[CH3:13])[NH:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 184721145-Chloro-3,4-difluoro-1,2-benzenediamine

Product 1

HCID 18472118HCID 18472118, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Chloro-3,4difluoro-1,2-phenylenediamine (11.6 g, crude material), isopropyl isothiocyanate (6.3 g, 62.1 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (28.0 g, 66.2 mmol) and pyridine (250 mL) were used according to general procedure I. The title compound was recrystallized from 1,4-dioxane to provide a tan solid (3.2 g, 25%); m.p. 175-178° C.; 1H NMR (DMSO-d6) δ: 11.0 (br s, 1H, NH), 7.07 (d, J=5.4 Hz, 1H, Ar—H), 6.96 (br s, 1H, NH), 3.93 (m, 1H, CH), 1.23 (d, J=6.5 Hz, 6H, overlapping CH3). Anal. Calcd. for C10H10F2ClN3-(0.6 C4H8O2): C, 49.89; H, 5.00; N, 14.08. Found: C, 50.29; H, 4.99; N, 14.47.

Workup

  1. customThe title compound was recrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-26a73fe75d9f48b1bfda65a90c3455d8
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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