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

HRID 1604428Notes

Reaction equation

HRID 1604428 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]>C(Cl)Cl>[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 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1,1'-carbonyldiimidazole (162.15 g) in CH2Cl2 (500 ml) was stirred on an ice-bath. 2,2-Dimethoxyethanamine (105.14 g) was added dropwise and the resulting reaction solution was stirred for 16 hours. The reaction mixture was cooled on ice, stirred for 30 minutes, and was allowed to crystallize. The precipitate was filtered off, stirred for 15 minutes in ethylacetate (250 ml) at RT, then cooled on an ice-bath for 30 minutes. The precipitate was filtered off, washed twice with DIPE (50 ml), then dried, yielding 137.4 g (69%) of N-(2,2-dimethoxyethyl)-1-H-imidazole-1-carboxamide (interm. 26).

Workup

  1. customthe resulting reaction solution
  2. stirringwas stirred for 16 hours
  3. temperatureThe reaction mixture was cooled on ice
  4. stirringstirred for 30 minutes
  5. customto crystallize
  6. filtrationThe precipitate was filtered off
  7. stirringstirred for 15 minutes in ethylacetate (250 ml) at RT
  8. temperaturecooled on an ice-bath for 30 minutes
  9. filtrationThe precipitate was filtered off
  10. washwashed twice with DIPE (50 ml)
  11. customdried

Sources & evidence

ORD record
ord-1d50e98925a5462b937ba53c79bac68e
Source dataset
uspto-grants-1999_11
Patent number
US05994376

Reaction notes

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