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Methane, dichloromethoxy- → HCID 18921503, compound

HRID 1654959
Notes
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Reaction equation

HRID 1654959 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 189215132-[(4-Chlorophenyl)sulfonylaminomethyl)indan

Product 1

HCID 18921503HCID 18921503, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. additionwas slowly added dropwise
  2. stirringstirred for 1 hour
  3. customThereafter, the organic phase was collected
  4. washwashed
  5. customdried
  6. customthe solvent was removed
  7. customThe residue was purified by silica gel column chromatography (chloroform)
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes