Methanethiol → 3-(Methylthio)pyruvaldehyde-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazone
Reaction equation
[Na].[CH3:2][SH:3].C[O-].[Na+].[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([Cl:18])[C:9]=1[NH:19][N:20]=[C:21]([CH2:24]Cl)[CH:22]=[O:23]>CO>[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([Cl:18])[C:9]=1[NH:19][N:20]=[C:21]([CH2:24][S:3][CH3:2])[CH:22]=[O:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
9.2 g of sodium was dissolved in 900 ml of methanol. 21.3 g of methanethiol was introduced into the sodium methylate solution thus obtained. Then 110.0 g of 3-chloropyruvaldehyde-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]hydrazone (produced according to Example 1) was added in portions at 30° to 40° C. The reaction mixture was stirred for 1 hour at 40° C. and then the methanol was distilled off in a water jet vacuum. The residue was mixed with 500 ml of water and extracted three times with 250 ml of dichloromethane each. The combined dichloromethane extracts were dried on sodium sulfate and concentrated by evaporation. The residue was suspended in 200 ml of n-hexane, filtered off and dried in a water jet vacuum. The yield of the product was 92.2 g [content (GC): 94.7 percent]. The melting point of the product was 88° to 90° C.
Workup
- customthus obtained
- distillationthe methanol was distilled off in a water jet vacuum
- additionThe residue was mixed with 500 ml of water
- extractionextracted three times with 250 ml of dichloromethane each
- dry with materialThe combined dichloromethane extracts were dried on sodium sulfate
- concentrationconcentrated by evaporation
- filtrationfiltered off
- dry with materialdried in a water jet vacuum
- customwas 88° to 90° C.
Sources & evidence
- ORD record
- ord-d4069e1577554c3c9d6b2cf6e71d9989
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05258523
Reaction notes
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