Hydrochloric Acid → N-[5-(4-Chlorophenyl)methyl-1,3-dioxan-2-yl]methylacetamide

HRID 1613329Notes

Reaction equation

HRID 1613329 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])=[CH:4][CH:3]=1.CO[CH:16](OC)[CH2:17][NH:18][C:19](=[O:21])[CH3:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]2[CH2:12][O:13][CH:16]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:11][CH2:10]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 150965432-(4-Chlorobenzyl)propane-1,3-diolHCID 15289457N-(2,2-Dimethoxyethyl)acetamide

Product 1

HCID 19775740N-[5-(4-Chlorophenyl)methyl-1,3-dioxan-2-yl]methylacetamideYield 30%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
75 °C

Procedure

4 g (20 mmol) of 2-[(4-chlorophenyl)methyl]propane-1,3-diol, 2.94 g (20 mmol) of N-(2,2-dimethoxyethyl)acetamide, 0.3 g of paratoluenesulphonic acid and 4 ml of diethyl ether saturated with hydrogen chloride are added to 150 ml of diethyl ether. The mixture is evaporated in vacuo, then 150 ml of benzene are added twice to the residue, it is heated to 70-80° C. under a slight vacuum and the solvent is evaporated. The residue is cooled, 150 ml of dichloromethane are added, and the solution is washed with a saturated solution of sodium hydrogen carbonate then with water and dried over magnesium sulphate. The residue is purified twice by chromatography on a silica gel column eluted with chloroform, and it is finally recrystallised in a 70:4 mixture of cyclohexane/ethyl acetate. 1.7 g (6 mmol) of product are obtained.

Workup

  1. customThe mixture is evaporated in vacuo
  2. addition150 ml of benzene are added twice to the residue, it
  3. customthe solvent is evaporated
  4. temperatureThe residue is cooled
  5. addition150 ml of dichloromethane are added
  6. washthe solution is washed with a saturated solution of sodium hydrogen carbonate
  7. dry with materialwith water and dried over magnesium sulphate
  8. customThe residue is purified twice by chromatography on a silica gel column
  9. washeluted with chloroform, and it
  10. customis finally recrystallised in a 70:4 mixture of cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-142aac11743945b08a226d4861578f0f
Source dataset
uspto-grants-1993_03
Patent number
US05192797

Reaction notes

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