Hydrochloric Acid → (1Z)-N-(4-Methoxyphenyl)-1-(methylsulfonyl)methanehydrazonoyl chloride
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Cl.[N:11]([O-])=O.[Na+].[Cl:15][CH2:16][S:17]([CH2:20]C(=O)C)(=[O:19])=[O:18].C([O-])(=O)C.[Na+]>O.CC(C)=O>[Cl:15]/[C:16](=[N:11]\[NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)/[S:17]([CH3:20])(=[O:19])=[O:18]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of p-anisidine (4.39 g, 3.6 mmol) in con. HCl (9.2 mL) and water (20 mL) at 0° C. was slowly added sodium nitrite (2.58 g, 3.7 mmol) in water (20 mL). The reaction mixture was stirred at 0° C. for 0.5 h. The above mixture was poured into a mixture of 3-chloromethanesulphonyl acetone (Grossert, J S, et. al., Can J. Chem. 1984, 62, 798)(6.1 g, 3.5 mmol), acetone (50 mL), sodium acetate (6.7 g, 8.2 mmol), and water (100 mL). The resulting mixture was stirred for 4 h at rt. The precipitate was filtered-off and dried to afford the hydrazone as a red solid (5.28 g, 57%); 1H NMR (CDCl3) δ: 8.05 (s, 1H), 7.12 (d, 2H), 6.91 (d, 2H), 3.80 (s, 3H), 3.23 (s, 3H) ppm.
Workup
- customat 0° C.
- stirringThe resulting mixture was stirred for 4 h at rt
- customdried
Sources & evidence
- ORD record
- ord-389a159f21a448aca6242fe34e531732
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06750225B2
Reaction notes
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