1,1'-Carbonyldiimidazole → 1H-Imidazole-1-carboxamide, N-(2,2-dimethoxyethyl)-

HRID 431069Notes

Reaction equation

HRID 431069 reaction equation
[C:1](N1C=CN=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17]>CCOC(C)=O>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH:17][C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 187633681H-Imidazole-1-carboxamide, N-(2,2-dimethoxyethyl)-Yield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,1′-carbonylbis[1H-imidazole] (2 mol) in EtOAc (800 ml) was stirred and cooled on an ice-bath, resulting in a suspension. 2,2-dimethoxyethanamine (2 mol) was added dropwise while the temperature was kept below 25 ° C. The resulting reaction mixture was stirred for 2 hours at RT, then for 30 minutes while cooling on an ice-bath. The precipitate was filtered off, stirred in EtOAc (400 ml) during 15 minutes, and on an ice-bath during 15 minutes. The precipitate was filtered off, washed with DIPE (2×50 ml), and dried, yielding 277 g (70%) of N-(2,2-dimethoxyethyl)-1H-imidazole-1-carboxamide (interm. 5).

Workup

  1. temperaturecooled on an ice-bath
  2. customresulting in a suspension
  3. customwas kept below 25 ° C
  4. customThe resulting reaction mixture
  5. stirringwas stirred for 2 hours at RT
  6. temperaturefor 30 minutes while cooling on an ice-bath
  7. filtrationThe precipitate was filtered off
  8. stirringstirred in EtOAc (400 ml) during 15 minutes
  9. filtrationThe precipitate was filtered off
  10. washwashed with DIPE (2×50 ml)
  11. customdried

Sources & evidence

ORD record
ord-28392dbf7be24a88957b82801723f1a0
Source dataset
uspto-grants-2003_12
Patent number
US06656959B1

Reaction notes

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