1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → N-isopropyl-1-methyl-5-nitro-1H-benzimidazol-2-amine

HRID 1391525Notes

Reaction equation

[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.[CH:13]([N:16]=[C:17]=S)([CH3:15])[CH3:14].CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1>N1C=CC=CC=1>[CH:13]([NH:16][C:17]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[N:12]=1)([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N1-methyl-4-nitro-benzene-1,2-diamine (2.0 g, 12.0 mmol) in pyridine (20 ml) was added isopropyl isothiocyanate (1.41 g, 13.2 mmol) and the mixture was heated to 90° C. After 1 h, 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (6.6 g, 15.6 mmol) was added and the mixture was heated at 90° C. After 16 h, the reaction mixture was cooled to rt, filtered and concentrated to a red residue. This was dissolved in EtOAc and washed with water (4×125 ml). The organic layer was dried over MgSO4 and concentrated to an orange solid. MeOH was added, and the solid was filtered and dried to give the title compound as an orange solid (2.4 g, 85%). 1H NMR (300 MHz, d6-DMSO) δ7.88 (dd, J=8.7 and 2.4 Hz), 7.30 (d, J=8.7 Hz, 1H), 6.89 (d, J=7.5 Hz, 1H), 4.08 (m, 1H), 3.56 (s, 3), 1.25 (d, J=6.6 Hz, 6H). MS (ESI) m/z=235 [M+H]+.

Workup

temperaturethe mixture was heated at 90° C
waitAfter 16 h
temperaturethe reaction mixture was cooled to rt
filtrationfiltered
concentrationconcentrated to a red residue
dissolutionThis was dissolved in EtOAc
washwashed with water (4×125 ml)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated to an orange solid
additionMeOH was added
filtrationthe solid was filtered
customdried

Sources & evidence

ORD record: ord-f671510ee94d4d79baffcc3a6d2d0b56
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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