1,2-Dichlorobenzene → HCID 21463598, compound

HRID 52207Notes

Reaction equation

[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12].[CH2:23]([C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([Cl:35])[CH:28]=1)[CH2:24][CH2:25][CH3:26].[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[CH2:23]([C:27]1[CH:34]=[CH:33][C:30]([C:31]2[N:2]([CH3:1])[N:3]=[C:4]([C:5]3[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=3[Cl:12])[N:32]=2)=[C:29]([Cl:35])[CH:28]=1)[CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 120 °C

Procedure

N-methyl-N-(phenylsulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (1.10 g), 4-butyl-2-chlorobenzonitrile (0.60 g) and anhydrous aluminum chloride (0.50 g) are added to o-dichlorobenzene (10 ml) and stirred at 120° C. for 1 hour. On completion of the reaction, chloroform (100 ml) is added and washed with dilute hydrochloric acid. After washing with water, the organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solution of hexane-ethyl acetate as eluent to give 0.70 g of compound (refractive index: 1.5667).

Workup

additionis added
washwashed with dilute hydrochloric acid
washAfter washing with water
dry with materialthe organic layer is dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe concentrate is purified by silica gel column chromatography
additionusing mixed solution of hexane-ethyl acetate as eluent

Sources & evidence

ORD record: ord-a927ab24f81441e1afffc927bc09bc20
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616594

Reaction notes

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