Dichloromethane → HCID 19936233, compound

HRID 36836Notes

Reaction equation

HRID 36836 reaction equation
[C:1]([O:5][C:6](=[O:23])[C:7]([CH2:18][S:19][CH2:20][CH2:21]O)([CH2:13][S:14][CH2:15][CH2:16]O)[CH2:8][S:9][CH2:10][CH2:11]O)([CH3:4])([CH3:3])[CH3:2].[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.ClCCl>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:23])[C:7]([CH2:18][S:19][CH2:20][CH2:21][S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31])([CH2:13][S:14][CH2:15][CH2:16][S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31])[CH2:8][S:9][CH2:10][CH2:11][S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 19936234HCID 19936234, compound

Product 1

HCID 19936233HCID 19936233, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of t-butyl-tris[(2-hydroxyethyl)thiomethyl]acetate (11.2 g, 0.029 mol) in 50 mL of pyridine is cooled to 0° C. and p-toluenesulfonyl chloride (18.3 g, 0.096 mol) is added in portions over 1 hr. The mixture is kept at 0° C. for 15 hrs. Then dichloromethane (200 mL) is added and the solution is washed four times with 100 mL of 10% hydrochloric acid, once with 100 mL of saturated sodium bicarbonate and once with 100 mL of water. The organic layer is dried over anhydrous sodium sulfate and evaporated to give t-butyl-tris[(2-tosylethyl)-thiomethyl]acetate.

Workup

  1. washthe solution is washed four times with 100 mL of 10% hydrochloric acid
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-9fd9ac66d9684d3c966fc5081d61a0d8
Source dataset
uspto-grants-1995_05
Patent number
US05417959

Reaction notes

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