Hydrochloric Acid → HCID 54354349, compound
Reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])[C:5]([O:7]C)=[O:6].Cl>[OH-].[K+]>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])[C:5]([OH:7])=[O:6]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5 g of 2-(2-chlorophenoxymethyl)-phenylglyoxylic acid methyl ester O-methyloxime in 50 ml of 1N aqueous KOH solution were refluxed for 2 hours. The mixture was cooled, after which the pH was brought to 1 with concentrated hydrochloric acid. The precipitate which separated out was filtered off under suction and dried. 4 g of 2-(2-chlorophenoxymethyl)-phenylglyoxylic acid O-methyloxime were obtained as a colorless solid, which was then dissolved in 50 ml of anhydrous dimethylformamide. 2.1 g of carbonyldiimidazole were added at -10° C. and stirring was carried out at this temperature for 2 hours. 0.89 g of sodium methanethiolate was then added and stirring was continued for a further 90 minutes at -10° C. and then for a further 90 minutes at room temperature. 100 ml of methylene chloride and 200 ml of saturated, aqueous sodium chloride solution were added, after which the organic phase was separated off and dried over magnesium sulfate and the solvent was removed under reduced pressure. 3.8 g of crude product were obtained. This was purified by flash chromatography over silica gel using hexane/ethyl acetate, 2.3 g of product being obtained as a yellow solid of melting point 58° to 60° C.
Workup
- temperatureThe mixture was cooled
- customThe precipitate which separated out
- filtrationwas filtered off under suction
- customdried
Sources & evidence
- ORD record
- ord-d034cdb6118b43a1850ccb611d54659f
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112860
Reaction notes
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