4-(1-Pyrrolidinyl)benzaldehyde → 4-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(4-pyrrolidinobenzylidene)thiosemicarbazide

HRID 1007279Notes

Reaction equation

HRID 1007279 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([C:18]2[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14]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:22][C:21]1[CH:20]=[CH:19][C:18]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 1040374-(1-Pyrrolidinyl)benzaldehydeHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 739967454-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(4-pyrrolidinobenzylidene)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, 0.6 mmol) and 4-pyrrolidinobenzaldehyde (126 mg, 0.72 mmol) similar to Example 3 and isolated as a white solid (60 mg, 29%). 1H NMR (CDCl3): 9.01 (s, 1H), 7.65 (s, 1H), 7.50-7.26 (m, 2H), 6.52 (d, J=8.8 Hz, 2H), 6.16 (ddd, J=8.1, 5.1, 2.7 Hz, 2H), 4.29 (t, J=8.1 Hz, 1H), 3.36-3.32 (m, 4H), 3.04 (s, 1H), 2.95 (s, 1H), 2.07-1.99 (m, 4H ), 1.87 (ddd, J=7.6, 7.0, 2.7 Hz, 1H), 1.63 (m, 1H), 1.53-1.38 (m, 2H).

Sources & evidence

ORD record
ord-9ff1191369f84d8d9a2036f0b7abffe1
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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