Methane, dichloromethoxy- → HCID 18921503, compound

HRID 1654959Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl[CH:27]([O:29]C)Cl>C(Cl)Cl>[CH:27]([C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[CH2:25][CH:17]([CH2:16][NH:15][S:12]([C:9]1[CH:8]=[CH:7][C:6]([Cl:5])=[CH:11][CH:10]=1)(=[O:14])=[O:13])[CH2:18]2)=[O:29]

Participants

Conditions

Temperature: -20 °C

Procedure

5.33 g (40.0 mmol) of anhydrous aluminum chloride was suspended in 20 ml of methylenechloride and added with 1.61 g (5.00 mmol) of 2-[(4-chlorophenyl)sulfonylaminomethyl]indan, followed by cooling at -20° C. 10 ml of methylene chloride containing as dissolved 0.68 ml (7.5 mmol) of dichloromethylmethylether was slowly added dropwise thereto, followed by stirring for 1 hour at the same temperature. The reaction solution was poured into ice-water and stirred for 1 hour. Thereafter, the organic phase was collected, washed, dried, and the solvent was removed. The residue was purified by silica gel column chromatography (chloroform), followed by recrystallizing from a solvent mixture of ethylacetate and hexane to obtain 375 mg of colorless crystals. Yield: 22%

Workup

additionwas slowly added dropwise
stirringstirred for 1 hour
customThereafter, the organic phase was collected
washwashed
customdried
customthe solvent was removed
customThe residue was purified by silica gel column chromatography (chloroform)
customby recrystallizing from a solvent mixture of ethylacetate and hexane

Sources & evidence

ORD record: ord-3a9d871d6eff468c92fee0e2b12d8ce2
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05409956

Reaction notes

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