Methyl chloroformate → HCID 11252029, compound

HRID 989433Notes

Reaction equation

HRID 989433 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH:6]([CH2:8][CH2:9][OH:10])[NH2:7].C(N(CC)CC)C>C(Cl)Cl>[NH2:7][N:6]([CH2:8][CH2:9][OH:10])[C:2](=[O:3])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 80172-HydrazinoethanolHCID 8471Triethylamine

Product 1

HCID 11252029HCID 11252029, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0-5° C., 248.4 g (2.628 mol) of methyl chloroformate were added with stirring, over a period of 30 min, to a mixture of 200 g (2.628 mol) of 2-hydrazinoethanol and 266 g (2.628 mol) of triethylamine in 1600 ml of methylene chloride. After 3 h of stirring at from 3 to 22 C, the resulting hydrochloride was removed by filtration and washed with THF. The filtrates were combined. The filter cake was suspended in 800 ml of THF and filtered again. This filtrate, too, was combined with the previous filtrate. The combined filtrates were concentrated under reduced pressure. This gave 366 g of the title compound as colorless oil having an HPLC purity of 95.3%, corresponding to a yield of 98.9% of theory. According to GC, the purity was 85.2%.

Workup

  1. customthe resulting hydrochloride was removed by filtration
  2. washwashed with THF
  3. filtrationfiltered again
  4. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc37f6e1d6324b21b776f2f644d631b8
Source dataset
uspto-grants-2003_10
Patent number
US06639070B1

Reaction notes

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