3-Pyridinecarboxaldehyde → 4-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(pyridin-3-ylmethylidene)thiosemicarbazide

HRID 1007262Notes

Reaction equation

HRID 1007262 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]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1>>[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:19][C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 28037864-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(pyridin-3-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 3-pyridine carboxaldehyde (53 μL, 0.56 mmol) similar to Example 3 and isolated as a white solid (59 mg, 39%). 1H NMR (CDCl3): 9.51 (s, 1H), 8.85 (d, J=1.8 Hz, 1H), 8.64 (dd, J=1.7, 5.0 Hz, 1H), 7.96-7.92 (m, 1H), 7.82 (s, 1H), 7.46 (d, J=6.3 Hz, 1H), 7.38-7.34 (m, 1H), 6.24-6.14 (m, 2H), 4.30-4.25 (m, 1H), 3.06 (s, 1H), 2.97 (s, 1H), 1.95-1.87 (m, 1H), 1.67 (d, J=8.7 Hz, 1H), 1.5 (d, J=9.0 Hz, 1H), 1.45-1.39 (m, 1H).

Sources & evidence

ORD record
ord-5b490439bb2742d2b3acfa4814c6a932
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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