Acetic Acid → HCID 18976546, compound

HRID 2393669Notes

Reaction equation

HRID 2393669 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][N:4]([CH2:8]CC#N)[C:3]1=[O:12].Cl.[C:14]([OH:17])(=[O:16])[CH3:15]>>[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][N:4]([CH2:8][CH2:15][C:14]([OH:17])=[O:16])[C:3]1=[O:12]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 18976536HCID 18976536, compound

Product 1

HCID 18976546HCID 18976546, compoundYield 50.4%

Procedure

334.33 g (2.0 mol) of 3-(3-methyl-2,4-dioxoimidazolidin-1-yl)propionitrile, prepared as described in Example 5, are hydrolysed for 5 hours and 30 minutes at 96°-107° C. in a mixture of 1482.7 g (13.0 mol) of aqueous 32% hydrochloric acid and 288.3 g (4.8 mol) of acetic acid. The reaction solution is then evaporated at 90° C. under reduced pressure in a rotary evaporator and dried at 120° C./0.1 mbar to constant weight, giving 354.1 g (95.1% of theory) of crude product, which is purified by recrystallization from 1 liter of ethyl acetate, giving 184 g (50.4% of theory) of crystalline 3-(3-methyl-2,4-dioxoimidazolidin-1-yl)propionic acid having a melting point of 109° C.

Workup

  1. customThe reaction solution is then evaporated at 90° C. under reduced pressure in a rotary evaporator
  2. customdried at 120° C./0.1 mbar to constant weight
  3. customgiving 354.1 g (95.1% of theory) of crude product, which
  4. customis purified by recrystallization from 1 liter of ethyl acetate

Sources & evidence

ORD record
ord-41954df988e7484491d29528d9731e49
Source dataset
uspto-grants-1998_09
Patent number
US05807927

Reaction notes

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