Dichloromethane → HCID 58380871, compound

HRID 45180Notes

Reaction equation

HRID 45180 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[F:5][C:6]1[C:7](C)=[C:8]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:9][N:10](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:11][CH:12](OC)OC.Cl[CH2:33]Cl>>[F:30][C:29]1[C:28]([CH3:33])=[C:27]2[C:8](=[CH:7][C:6]=1[F:5])[CH:9]=[N:10][CH:11]=[CH:12]2

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 6451240Aluminum(III) ChlorideHCID 67072557HCID 67072557, compound

Product 1

HCID 58380871HCID 58380871, compound

Conditions

Temperature
50 °C

Procedure

Aluminium trichloride (112 g, 838 mmol) was suspended in dichloromethane (250 mL) at 0° C. A solution of N-(3,4-difluoro-2-methylbenzyl)-N-(2,2-dimethoxyethyl)-4-methylphenyl-sulphonylamine (42, 68.3 g) in dichloromethane (250 mL) was added. The reaction mixture was heated at 50° C. for 2 hours, before being cooled to 0° C. and poured on ice. The organic layer was separated, and the aqueous layer extracted twice more with dichloromethane/isopropanol (3:1). The combined organic phase was extracted twice with saturated sodium bicarbonate solution and dried over magnesium sulphate, before filtration and evaporation gave 63.5 g of crude dark brown semi-solid product. This was purified by chromatography on silica gel. Elution with ethyl acetate/heptane (5%:95% to 35%:65%) gave 11.3 g of the title compound 43 as a tan-coloured solid. Rt=0.86 min (Method 10). Detected mass: 180.1 (M+H+).

Workup

  1. temperaturebefore being cooled to 0° C.
  2. additionpoured on ice
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted twice more with dichloromethane/isopropanol (3:1)
  5. extractionThe combined organic phase was extracted twice with saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulphate, before filtration and evaporation
  7. customgave 63.5 g of crude dark brown semi-solid product
  8. customThis was purified by chromatography on silica gel
  9. washElution with ethyl acetate/heptane (5%:95% to 35%:65%)

Sources & evidence

ORD record
ord-21088373b2164c4694968c344a697d73
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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