Ammonia → 2-[2-(4-Methylbenzene-1-sulfonyl)ethyl]-1,3-dioxolane

HRID 1073836Notes

Reaction equation

HRID 1073836 reaction equation
O.[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].Br[CH2:14][CH2:15][CH:16]1[O:20][CH2:19][CH2:18][O:17]1.N>CN(C=O)C>[CH2:19]1[O:20][CH:16]([CH2:15][CH2:14][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:11])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[O:17][CH2:18]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 236829571011708-74-9

Product 1

HCID 125389982-[2-(4-Methylbenzene-1-sulfonyl)ethyl]-1,3-dioxolaneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium 4-toluenesulphinate monohydrate (37.2 g, 0 19 mole) and 2-(2-bromoethyl)-1,3-dioxolane (20 ml, 0.17 mole) in dry DMF (100 ml) was stirred at room temperature for 64 h, resulting in a homogenous solution. This was poured into ice/water (1 liter) containing conc. ammonia solution (100 ml) and stirred vigorously until a white precipitate formed. The solid was filtered off, washed with water, dried and recrystallised from propan-2-ol/ether to give the title compound (D24) as a white solid (28.7 g, 66%) m.p. 78-80° C.. 1H-NMR (CDCl3) δ:

Workup

  1. customresulting in a homogenous solution
  2. stirringstirred vigorously until a white precipitate
  3. customformed
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallised from propan-2-ol/ether

Sources & evidence

ORD record
ord-16b1c3f5a8994225aca937d5c370a2f6
Source dataset
uspto-grants-1990_11
Patent number
US04971975

Reaction notes

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