5-Nitrofurfural → 4-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(5-nitro-furan-2-ylmethylidene)thiosemicarbazide

HRID 1007264Notes

Reaction equation

HRID 1007264 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[O:20][C:19]([CH:21]=O)=[CH:18][CH:17]=1)([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:21][C:19]1[O:20][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 127745-NitrofurfuralHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 865873644-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(5-nitro-furan-2-ylmethylidene)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 5-nitro-2-furaldehyde (59 μL, 0.56 mmol) similar to Example 3 and isolated as a dark yellow solid (4 mg, 2%). 1H NMR (CDCl3): 10.02 (s, 1H), 7.74 (s, 1H), 7.50 (d, J=7.2 Hz, 1H), 7.39 (d, J=3.9 Hz, 1H), 6.88 (d, J=3.9, 1H), 6.26-6.14 (m, 2H), 4.26-4.22 (m, 1H), 3.07 (s, 1H), 2.99 (s, 1H), 1.94-1.87 (m, 1H), 1.68 (d, J=9.3 Hz, 1H), 1.51 (d, J=9.0 Hz, 1H), 1.48-1.42 (m, 1H).

Sources & evidence

ORD record
ord-bae0651a07d74f63922d0abce492770f
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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