4-Nitrobenzaldehyde → HCID 2803290, compound

HRID 1007259Notes

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][C:19]([CH:20]=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:20][C:19]1[CH:22]=[CH:23][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1

Participants

Reactant 2

HCID 5414-Nitrobenzaldehyde

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

Product 1

HCID 2803290HCID 2803290, compound

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-nitrobenzaldehyde (85 mg, 0.56 mmol) similar to Example 3 and isolated as a yellow solid (84 mg, 47%). 1H NMR (CDCl3): 9.80 (s, 1H), 8.28 (d, J=9.0 Hz, 2H), 7.90 (s, 1H), 7.78 (d, J=8.7 Hz, 2H), 7.47 (d, J=7.2 Hz, 1H), 6.26-6.14 (m, 2H), 4.30-4.26 (m, 1H), 3.08 (s, 1H), 2.99 (s, 1H), 1.96-1.89 (m, 1H), 1.70 (d, J=9.0 Hz, 1H), 1.51 (d, J=9.0 Hz, 1H), 1.47-1.41 (m, 1H).

Sources & evidence

ORD record: ord-c5df97c406054cd587b852da0f39d697
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794400B2

Reaction notes

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