1,2-Dichlorobenzene → HCID 19021369, compound

HRID 1108947Notes

Reaction equation

[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[CH2:22]([C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[Cl:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]1[N:40]=[C:39]([C:38]2[CH:41]=[CH:42][C:35]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:36][CH:37]=2)[N:2]([CH3:1])[N:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 0.82 g of N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride, 0.70 g of 4-tridecylbenzonitrile, 0.4 g of anhydrous aluminium chloride and 3 ml of o-dichlorobenzene was stirred in an oil bath at a temperature of 140° C. for 30 minutes. After the cooling, the resulting solution was dissolved in 100 ml of chloroform, washed with diluted hydrochloric acid solution, diluted sodium hydroxide solution and saline water in this order, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 0.70 g of the given compound (melting point: 55.0°-57.0° C.).

Workup

washwashed with diluted hydrochloric acid solution, diluted sodium hydroxide solution and saline water in this order
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under a reduced pressure
concentrationThe resulting concentrate
customwas purified through a chromatography of silica gel column

Sources & evidence

ORD record: ord-b8070fc3902840f599ddd23c266438b8
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05318959

Reaction notes

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