1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → HCID 18472082, compound

HRID 2227181Notes

Reaction equation

HRID 2227181 reaction equation
[F:1][C:2]1[C:3]([NH2:11])=[C:4]([NH2:10])[CH:5]=[C:6]([F:9])[C:7]=1[F: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>[F: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]([F:9])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 27739583,4,5-Trifluorobenzene-1,2-diamine

Product 1

HCID 18472082HCID 18472082, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4,5-Trifluoro-1,2-phenylenediamine (6.0 g, 31.2 mmol), isopropyl isothiocyanate (3.6 g, 35.6 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (17.0 g, 40.1 mmol) and pyridine (225 mL) were used according to general procedure I. The title compound was recrystallized from 1,4-dioxane to provide a white solid (4.07 g, 57%); m.p. 182-184° C.; 1H NMR (DMSO-d6) δ: 10.97 (br s, 1H, NH), 7.01 (m, 1H, Ar—H), 6.80 (br s, 1H, NH), 3.91 (m, 1H, CH), 1.20 (d, J=6.4 Hz, 6H, overlapping CH3).

Workup

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

Sources & evidence

ORD record
ord-538d22790d8d46759cec010c4e94e4cd
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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