5-Nitrothiophene-2-carboxaldehyde → HCID 86587363, compound

HRID 1007263Notes

Reaction equation

HRID 1007263 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[S: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[S:20][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 782815-Nitrothiophene-2-carboxaldehydeHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 86587363HCID 86587363, 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 5-nitrothiophene-2-carboxaldehyde (88 mg, 0.56 mmol) similar to Example 3 and isolated as an orange solid (67 mg, 37%). 1H NMR (CDCl3): 10.13 (s, 1H), 7.96 (s, 1H), 7.86 (d, J=4.2 Hz, 1H), 7.37 (d, J=7.5 Hz, 1H), 7.17 (d, J=4.2 Hz, 1H), 6.26-6.13 (m, 2H), 4.26-4.20 (m, 1H), 3.05 (s, 1H), 3.00 (s, 1H), 1.95-1.87 (m, 1H), 1.70 (d, J=9.0 Hz, 1H), 1.49 (d, J=9.0 Hz, 1H), 1.46-1.39 (m, 1H).

Sources & evidence

ORD record
ord-22adb07e2126445a93903e761cc6cc8b
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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