1,1'-Carbonyldiimidazole → HCID 57939588, compound

HRID 1436904Notes

Reaction equation

HRID 1436904 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[CH2:6][NH:7][CH2:8][CH2:9][O:10][CH3:11].[C:21](N1C=CN=C1)([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=[O:22]>C1(C)C=CC=CC=1.C(Cl)Cl>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:14]=1)[CH2:6][N:7]([CH2:8][CH2:9][O:10][CH3:11])[C:21]([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=[O:22]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 81653569HCID 81653569, compound

Product 1

HCID 57939588HCID 57939588, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

In a mixed solution of 37 ml of toluene and 4 ml of methylene chloride was dissolved 2.76 g of 3,5-bistrifluoromethylbenzyl-2-methoxyethylamine, added thereto was 1.78 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at 60° C. for 3 hours. To the reaction mixture was added distilled water, and extracted with chloroform. The organic layer was dried over magnesium sulfate, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:acetone=9:1→2:1), to give 3.45 g of imidazole-1-carboxylic acid 3,5-bistrifluoromethylbenzyl-2-methoxyethylamide as shown in Table 133 below.

Workup

  1. additionadded
  2. additionTo the reaction mixture was added
  3. distillationdistilled water
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:acetone=9:1→2:1)

Sources & evidence

ORD record
ord-06cca6b8a4c04a7e877da10bcaad9c7f
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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