(2,4-Dichlorophenoxy)acetyl chloride → 3-[(1-Ethylpropyl)amino]-6-methyl-2,4-dinitrobenzyl (2,4-dichlorophenoxy)acetate

HRID 1388079

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

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-35a06acdc4b8426fbb81651fdf2f46c2
Source dataset: uspto-grants-1984_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04430114

Linked notes

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