Benzaldehyde → HCID 85068553, compound

HRID 1007254Notes

Reaction equation

HRID 1007254 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].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+]>C(O)C.O>[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:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 517045Sodium AcetateHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 85068553HCID 85068553, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide (100 mg, 0.55 mmol) and benzaldehyde (56 μl, 0.55 mmol) in ethanol (5 mL) was added a solution of sodium acetate (45 mg, 0.55 mmol) in water (1 mL) and the mixture was stirred at room temperature for 24 h. The mixture was diluted with water (1.5 mL) and the resultant precipitate was collected by filtration and isolated as a white solid (14 mg, 9%). 1H NMR (CDCl3): 9.84 (s, 1H), 7.88 (s, 1H), 7.64-7.61 (m, 2H), 7.50 (d, J=7.5 Hz, 1H), 7.42-7.40 (m, 3H), 6.24-6.14 (m, 2H), 4.314.26 (m, 1H), 3.06 (s, 1H), 2.96 (s, 1H), 1.94-1.86 (m, 1H), 1.67 (d, J=9.3 Hz, 1H), 1.52 (d, J=9.0 Hz, 1H), 1.46-1.39 (m, 1H).

Workup

  1. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-237f3e626c1c4d94aeaff0862c7d6f47
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

Loading…