1,1'-Carbonyldiimidazole → HCID 18976548, compound

HRID 2393665Notes

Reaction equation

HRID 2393665 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1([CH3:26])[C:18](=[O:19])[N:17]([CH2:20][CH2:21][C:22]([OH:24])=O)[C:16](=[O:25])[NH:15]1.[CH3:27][O:28][CH:29]([O:32][CH3:33])[CH2:30][NH2:31]>O1CCCC1>[CH3:27][O:28][CH:29]([O:32][CH3:33])[CH2:30][NH:31][C:22](=[O:24])[CH2:21][CH2:20][N:17]1[C:18](=[O:19])[C:14]([CH3:13])([CH3:26])[NH:15][C:16]1=[O:25]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 89728Aminoacetaldehyde dimethyl acetalHCID 31541733-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)propanoic acid

Product 1

HCID 18976548HCID 18976548, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Analogously to Example 1, 165.43 g (1.02 mol) of 1,1'-carbonyldiimidazole and 700 ml of tetrahydrofuran are introduced into an apparatus, allowed to react with 202.86 g (1.0 mol) of 3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)propionic acid and subsequently reacted with 107.21 g (1.02 mol) of 2-aminoacetaldehyde dimethyl acetal. The reaction mixture is evaporated to dryness at 80° C./0.1 mbar in a rotary evaporator, and the resultant residue is purified analogously to Example 1, giving 154.2 g (54.2% of theory) of N-(2,2-dimethoxyethyl)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)propionamide, which melts at 123° C.

Workup

  1. customThe reaction mixture is evaporated to dryness at 80° C./0.1 mbar
  2. customin a rotary evaporator
  3. customthe resultant residue is purified analogously to Example 1

Sources & evidence

ORD record
ord-5845e108aa2d4ecd8284468219deed88
Source dataset
uspto-grants-1998_09
Patent number
US05807927

Reaction notes

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