Pyridine → 1-Chloroethyl bis(2-methoxyethyl)carbamate

HRID 882351Notes

Reaction equation

HRID 882351 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][CH3:9].N1C=CC=CC=1.[C:16](Cl)(=[O:21])[O:17][CH:18]([Cl:20])[CH3:19]>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][CH3:9])[C:16](=[O:21])[O:17][CH:18]([Cl:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2383Bis(2-Methoxyethyl)amineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 866962971-Chloroethyl bis(2-methoxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution of bis(2-methoxyethyl)amine (1.94 g, 14.5 mmol, Aldrich) and pyridine (1.26 g, 1.29 mL, 15.9 mmol) in methylene chloride (18 mL) at −78° C., was added slowly 1-chloroethyl carbonochloridate (1.98 g, 1.5 mL, 13.8 mmol, Aldrich) over ˜15 min. The reaction mixture was allowed to stir at −78° C. for 3 h, giving a white precipitate. This cold reaction mixture was filtered to remove the solid and the filtrate was concentrated to dryness, giving the crude 1-chloroethyl bis(2-methoxyethyl)carbamate used for the next step without further purification.

Workup

  1. customgiving a white precipitate
  2. customThis cold reaction mixture
  3. filtrationwas filtered
  4. customto remove the solid
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-7251f1e9b7064413960d88be98365ece
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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