4-Nitroperoxybenzoic acid → 4-Nitrobenzoic Acid
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12]O)=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2].ClC(Cl)(Cl)C1N(C(=O)C(Cl)Cl)CCS1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 22 g (0.12 mole) of 90% p-nitroperbenzoic acid in 500 ml of methylene chloride is slowly added, while maintaining the temperature between -5° C. and -10° C., to a solution of 31.7 g (0.1 mole) of 2-trichloromethyl-3-dichloroacetyl-1,3 thiazolidine in 200 ml of methylene chloride. The addition is carried out with stirring. Then the reaction mixture is stirred for 4 further hours, the temperature being ambient. Then the reaction mixture is cooled to 0° C. and the p-nitrobenzoic acid which has formed is separated by filtration. The filtrate is washed with a dilute aqueous solution of sodium carbonate, then with water. After separation the organic phase is dried on sodium sulfate. The methylene chloride is removed by distillation under vacuum. 31.5 g (yield 94%) of 1-oxo-2-trichloromethyl-3-dichloroacetyl-1,3-thiazolidine, which is white solid melting at 140° C., is thus obtained. The structure of the product is confirmed by the infra-red and elemental analysis:
Workup
- temperaturewhile maintaining the temperature between -5° C. and -10° C.
- additionThe addition
- stirringThen the reaction mixture is stirred for 4 further hours
Sources & evidence
- ORD record
- ord-5d81663b8ea04ffea1e8986d6a70a145
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04197110
Reaction notes
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