(2,4-Dichlorophenoxy)acetyl chloride → 3-[(1-Ethylpropyl)amino]-6-methyl-2,4-dinitrobenzyl (2,4-dichlorophenoxy)acetate
Reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[C:8]([N+:19]([O-:21])=[O:20])=[C:9]([C:12]([CH3:18])=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[CH2:10][OH:11])[CH2:4][CH3:5])[CH3:2].[Cl:22][C:23]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:24]=1[O:25][CH2:26][C:27](Cl)=[O:28]>C1C=CC=CC=1.CCOCC>[Cl:22][C:23]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:24]=1[O:25][CH2:26][C:27]([O:11][CH2:10][C:9]1[C:12]([CH3:18])=[CH:13][C:14]([N+:15]([O-:17])=[O:16])=[C:7]([NH:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:8]=1[N+:19]([O-:21])=[O:20])=[O:28]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
3-[(1-Ethylpropyl)amino]-6-methyl-2,4-dinitrobenzyl alcohol (2.0 g; 0.007 mol) and 2,4-dichlorophenoxyacetyl chloride (used in excess over theory) are dissolved in benzene, and the solution stirred at 60° C. until tlc (silica gel-benzene) indicates the reaction to be complete. The reaction mixture is then cooled down, diluted with ether, and washed with dilute sodium bicarbonate solution until the washings became alkaline. The organic layer is then separated, dried over magnesium sulfate, and evaporated to afford a liquid residue, which solidifies gradually (3.3 g; 94%). Recrystallization of this solid from methanol affords 1.4 g of title product, melting point 103°-106° C.
Workup
- customthe reaction
- temperatureThe reaction mixture is then cooled down
- washwashed with dilute sodium bicarbonate solution until the washings
- customThe organic layer is then separated
- dry with materialdried over magnesium sulfate
- customevaporated
- customto afford a liquid residue, which
- customRecrystallization of this solid from methanol
Sources & evidence
- ORD record
- ord-9628261b2ef74f75acc4733df6964e9f
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04288385
Reaction notes
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