Benzyl bromoacetate → HCID 20262548, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([O-:19])=[O:18].[Na+].Br[CH2:22][C:23]([O:25]CC1C=CC=CC=1)=[O:24]>CN(C=O)C>[C:23]([O:25][O:18][C:17](=[O:19])[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])(=[O:24])[CH3:22]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
50 g (0.166 moles) of sodium 2-[(2,6-dichlorophenyl)amino]phenylacetate were dissolved in 200 ml of N,N'-dimethylformamide under heating to 50° C., and 41.620 g (0.181 moles) of benzyl bromoacetate were added thereto. Under these conditions stirring was continued for 3 hours. Upon completion of the reaction, the solvent was removed at reduced pressure and the sodium salts were precipitated with addition of 400 ml of ether. The solution was then filtered and the ether phase was washed three times with 100 ml of water and dried on sodium sulphate. The resulting product was concentrated until an oil was obtained, which oil was washed twice with 100 ml of hexane and then crystallized with methanol, thus obtaining 45.28 (61%) of 2-[(2,6-dichlorophenyl)amino]phenylacetoxy acetate.
Workup
- customUpon completion of the reaction
- customthe solvent was removed at reduced pressure
- customthe sodium salts were precipitated with addition of 400 ml of ether
- filtrationThe solution was then filtered
- washthe ether phase was washed three times with 100 ml of water
- customdried on sodium sulphate
- concentrationThe resulting product was concentrated until an oil
- customwas obtained
- washwhich oil was washed twice with 100 ml of hexane
- customcrystallized with methanol
Sources & evidence
- ORD record
- ord-d70259c471e94f81804063fc88cd6c41
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04548952
Reaction notes
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