Methyl isothiocyanate → N,1-dimethyl-5-nitro-1H-1,3-benzodiazol-2-amine

HRID 1391529Notes

Reaction equation

HRID 1391529 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.[CH3:13][N:14]=[C:15]=S>>[CH3:13][NH:14][C:15]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

Participants

3

Reactant 2

HCID 11167Methyl isothiocyanateHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 53396494N,1-dimethyl-5-nitro-1H-1,3-benzodiazol-2-amineYield 53.3%

Procedure

N1-methyl-4-nitro-benzene-1,2-diamine (2.0 g, 12.0 mmol) and methyl isothiocyanate (0.90 ml, 13.2 mmol) were coupled using the procedure of example one part B to give the title compound as a yellow solid (1.32 g, 53%). 1H NMR (300 MHz, d6-DMSO) δ 7.98 (d, J=2.1 Hz, 1H), 7.90 (dd, J=8.7 and 2.4 Hz, 1H), 7.32 (d, J=8.7 Hz, 1H), 7.15 (m, 1H), 3.55 (d, 3H), 2.95 (d, J=4.5 Hz, 3H).

Sources & evidence

ORD record
ord-2b62eb0a71c241b49e0e78788fa11c8b
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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