2-Nitrobenzaldehyde → 4-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(2-nitrobenzylidene)thiosemicarbazide

HRID 1007266Notes

Reaction equation

HRID 1007266 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[NH:8][C:9]([NH:11][NH2:12])=[S:10].[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O)([O-:15])=[O:14]>>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[NH:8][C:9](=[S:10])[NH:11][N:12]=[CH:18][C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[N+:13]([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 865873664-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(2-nitrobenzylidene)thiosemicarbazide

Procedure

The title compound was prepared from a mixture of N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide (100 mg, 0.56 mmol) and 2-nitrobenzaldehyde (85 mg, 0.56 mmol) similar to Example 3 and isolated as a yellow solid (20 mg, 11%). 1H NMR (CDCl3): 9.37 (s, 1H), 8.27 (s, 1H), 8.00 (d, J=8.1 Hz, 1H), 7.89 (d, J=7.5 Hz, 1H), 7.68 (t, J=7.5 Hz, 1H), 7.57 (t, J=7.8 Hz, 1H), 7.43 (d, J=7.2 Hz, 1H), 6.24-6.14 (m, 2H), 4.30-4.26 (m, 1H), 3.07 (s, 1H), 2.97 (s, 1H), 1.94-1.86 (m, 1H), 1.67 (d, J=8.4 Hz, 1H), 1.52 (d, J=9.0 Hz, 1H), 1.46-1.40 (m, 1H).

Sources & evidence

ORD record
ord-76c62a115b9c456ebde210b6145052b7
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

Loading…