Acetic Acid → HCID 73996737, compound

HRID 1007256Notes

Reaction equation

HRID 1007256 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][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.C(O)(=O)C>C(O)C>[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][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 73996737HCID 73996737, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide (100 mg, 0.56 mmol), p-anisaldehyde (69 μL, 0.56 mmol) and glacial acetic acid (31 μl) in ethanol (5 mL) was stirred at room temperature for 1 h. The resultant precipitate was collected by filtration and isolated as a white solid (100 mg, 59%). 1H NMR (CDCl3): 9.05 (s, 1H), 7.72 (s, 1H), 7.57 (d, J=8.7 Hz, 2H), 7.44 (d, J=6.9 Hz, 1H), 6.93 (d, J=8.7 Hz, 2H), 6.23-6.14 (m, 2H), 4.30-4.26 (m, 1H), 3.85 (s, 3H), 3.06 (s, 1H), 2.96 (s, 1H), 1.94-1.86 (m, 1H), 1.67 (d, J=9.0 Hz, 1H), 1.51 (d, J=9.0 Hz, 1H), 1.45-1.40 (m, 1H).

Workup

  1. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-d8c62b290db64f2684d238aa42e463a3
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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