Cyclohexyl isothiocyanate → HCID 59674133, compound

HRID 1391538Notes

Reaction equation

HRID 1391538 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]1([N:19]=[C:20]=S)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH:13]1([NH:19][C:20]2[N:2]([CH3:1])[C:3]3[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=3[N:12]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 14289Cyclohexyl isothiocyanateHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 59674133HCID 59674133, compoundYield 73.2%

Procedure

N1-methyl-4-nitro-benzene-1,2-diamine (2.0 g, 12.0 mmol) and cylcohexyl isothiocyanate (1.80 ml, 13.2 mmol) were coupled using the procedure of intermediate example one part B to give the title compound as a yellow solid (2.41 g, 73%). 1H NMR (300 MHz, d6-DMSO) δ 7.98 (d, J=2.4 Hz, 1H), 7.88 (dd, J=8.7 and 2.4 Hz, 1H), 7.30 (d, J=8.7 Hz, 1H), 6.88 (d, J=7.8 Hz, 1H), 3.74 (m, 1H), 3.56 (s, 3H), 2.00 (M, 2H), 1.75 (m, 2H), 1.63 (m, 1H), 1.25-1.36 (M, 4H), 1.17 (M, 1H) ppm.

Sources & evidence

ORD record
ord-99439c2d2b564c329a18325ebfaf0b76
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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