Dichloromethane → HCID 12803013, compound

HRID 1834042Notes

Reaction equation

HRID 1834042 reaction equation
[OH-].[Na+].[CH:3]1([NH:8][S:9]([CH2:12][Br:13])(=[O:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:14][C:15]([Cl:21])([S:19]Cl)[CH:16]([Cl:18])[Cl:17].ClCCl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH:3]1([N:8]([S:19][C:15]([Cl:21])([Cl:14])[CH:16]([Cl:18])[Cl:17])[S:9]([CH2:12][Br:13])(=[O:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 14798Sodium HydroxideHCID 12803012HCID 12803012, compound

Product 1

HCID 12803013HCID 12803013, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
0 °C

Procedure

A 5.76 g (0.072 mol) 50% aqueous solution of sodium hydroxide was added slowly to a solution of 8.6 g (0.036 mol) N-cyclopentyl bromomethanesulfonamide, 8.6 g (0.036 mol) 1,1,2,2-tetrachloroethylsulfenyl chloride, and about 0.1 g benzyltriethyl ammonium chloride in 200 mol dichloromethane cooled to 0° C with an ice bath. The reaction mixture was then stirred at 0° C for 2 hours, washed with water, dried over magnesium sulfate and evaporated to give a brown oil. The oil was chromatography over silica gel with dichloromethane/petroleum-ether elution to give 5.5 g (35% yield) of the product, as a grey solid, m.p. 59°-60° C. The elemental analysis for the product is tabulated in Table I under compound No. 9.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customto give a brown oil
  5. washwith dichloromethane/petroleum-ether elution

Sources & evidence

ORD record
ord-6f147786807f4c49bc0eb5380ca9a050
Source dataset
uspto-grants-1978_01
Patent number
US04068000

Reaction notes

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