1,1'-Carbonyldiimidazole → HCID 18976547, compound

HRID 2393666Notes

Reaction equation

HRID 2393666 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][N:14]1[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[N:16]([CH2:22][CH2:23][C:24]([OH:26])=O)[C:15]1=[O:27].[CH3:28][O:29][CH:30]([O:33][CH3:34])[CH2:31][NH2:32]>O1CCCC1>[CH3:28][O:29][CH:30]([O:33][CH3:34])[CH2:31][NH:32][C:24](=[O:26])[CH2:23][CH2:22][N:16]1[C:17]([CH3:20])([CH3:21])[C:18](=[O:19])[N:14]([CH3:13])[C:15]1=[O:27]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 89728Aminoacetaldehyde dimethyl acetalHCID 18976539HCID 18976539, compound

Product 1

HCID 18976547HCID 18976547, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

82.7 g (0.51 mol) of 1,1'-carbonyldiimidazole in 5.0 l of tetrahydrofuran are allowed to react as described in Example 1, with 93.08 g (0.5 mol) of 3-(3,5,5-trimethyl-2,4-dioxoimidazolidin-1-yl)propionic acid and are subsequently reacted with 53.62 g (0.51 mol) of 2-aminoacetaldehyde dimethyl acetal. The reaction mixture is evaporated in a rotary evaporator, and the imidazole present in the residue is removed by distillation at a bath temperature of 120° C./0.1 mmHg for 3 hours, giving 134.1 g (98.1% of theory) of a brownish, liquid crude product, which is recrystallized from 130 ml of ethyl acetate, giving 88.1 g (65.0% of theory) of colourless, crystalline N-(2,2-di methoxyethyl)-3-(3,5,5-trimethyl-2,4-dioxoimidazolidin-1-yl)propionamide, whose melting point is 86.4° C.

Workup

  1. customto react
  2. customThe reaction mixture is evaporated in a rotary evaporator
  3. customthe imidazole present in the residue is removed by distillation at a bath temperature of 120° C./0.1 mmHg for 3 hours
  4. customgiving 134.1 g (98.1% of theory) of a brownish, liquid crude product, which
  5. customis recrystallized from 130 ml of ethyl acetate

Sources & evidence

ORD record
ord-2fc8afd932ff43a5a5de55dcfa35939b
Source dataset
uspto-grants-1998_09
Patent number
US05807927

Reaction notes

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