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

HRID 1007258Notes

Reaction equation

HRID 1007258 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].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=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:18][C:17]1[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 739967464-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(4-chlorobenzylidene)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 4-chlorobenzaldehyde (79 mg, 0.56 mmol) similar to Example 3 and isolated as a white solid (68 mg, 40%). 1H NMR (CDCl3): 9.15 (s, 1H), 7.73 (s, 1H), 7.56 (d, J=8.4 Hz, 2H), 7.44 (s, 1H), 7.39 (d, J=8.7 Hz, 2H), 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), 1.68 (d, J=9.0 Hz, 1H), 1.51 (d, J=9.0 Hz, 1H), 1.45-1.39(m, 1H).

Sources & evidence

ORD record
ord-504aff9a9b54405e8bedcf5923eb3409
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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