Hydrochloric Acid → HCID 19755076, compound

HRID 1589046Notes

Reaction equation

HRID 1589046 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5]([CH3:8])([CH3:7])[CH2:4][O:3]1.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>ClCCl>[CH3:1][C:2]1([CH3:9])[N:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([CH3:8])([CH3:7])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 641504oxazolidine, 2,2,4,4-tetramethyl-

Product 1

HCID 19755076HCID 19755076, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.11 g (100.0 mmol) of 2,2,4,4-tetramethyl-1,3-oxazolidine (can also be employed in the form of the mixed fraction) were added gradually at room temperature to a solution of 5.43 g (50.0 mmol) of ethyl chloroformate in 50 ml of dry dichloromethane. After stirring for 16 hours, the reaction mixture was poured into 40 ml of 2N HCl. The phases were separated, the aqueous phase was extracted three times with 20 ml of ether each time and the combined organic phases were deacidified and dried over solid sodium hydrogen sulphate and sodium sulphate in the amount ratio 1:2. After the removal of the solvent in vacuo at a maximum of 100 mbar/40° C. bath temperature, the crude product was distilled under reduced pressure. 8.05 g (80%) of the title compound were obtained as a colorless liquid of b.p.: 87° C./10 mbar and RF =0.61 (silica gel, ether/pentane 1:1).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted three times with 20 ml of ether each time
  3. dry with materialdried over solid sodium hydrogen sulphate and sodium sulphate in the amount ratio 1:2
  4. customAfter the removal of the solvent in vacuo at a maximum of 100 mbar/40° C. bath temperature
  5. distillationthe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-7c45b1ff40314fef83678ef0e5785d0c
Source dataset
uspto-grants-1993_06
Patent number
US05223633

Reaction notes

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