1,1-Dichloroethane → 2-hydroxy-6-(N,N-diethylsulfamoyl)-1-naphthaldehyde

HRID 542160Notes

Reaction equation

ClC(Cl)C.[OH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH:16]=[O:17].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:22]([N:24]([CH2:29][CH3:30])[S:25](Cl)(=[O:27])=[O:26])[CH3:23]>C(Cl)Cl>[OH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:25](=[O:27])(=[O:26])[N:24]([CH2:29][CH3:30])[CH2:22][CH3:23])[CH:12]=2)[C:7]=1[CH:16]=[O:17]

Participants

Conditions

Temperature: 50 °C

Procedure

600 ml of a dichloroethane solution containing 150 g (0.87 mole) of 2-hydroxy-1-naphthaldehyde and 250 g (1.87 moles) of anhydrous aluminum chloride was stirred with heating at 50° C. To the solution was added dropwise 172.2 g (1 mole) of N,N-diethylsulfamoyl chloride. After the completion of the dropwise addition, the mixture was refluxed for 3 hours. After cooling to room temperature, the reaction mixture was poured into 1 liter of ice water. Methylene chloride was added to the mixture and it was extracted and separated. The organic layer was concentrated to about 500 ml. To the concentrate was added methanol to precipitate crystals. The precipitated crystals were collected by filtration, and washed with methanol to obtain 228 g (0.74 mole) of 2-hydroxy-6-(N,N-diethylsulfamoyl)-1-naphthaldehyde.

Workup

additionAfter the completion of the dropwise addition
temperaturethe mixture was refluxed for 3 hours
temperatureAfter cooling to room temperature
extractionwas extracted
customseparated
concentrationThe organic layer was concentrated to about 500 ml
additionTo the concentrate was added methanol
customto precipitate crystals
filtrationThe precipitated crystals were collected by filtration
washwashed with methanol

Sources & evidence

ORD record: ord-e42e8213cb5e424e8aee0d6d7b80940a
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04656126

Reaction notes

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