1,1'-Carbonyldiimidazole → HCID 178519095, compound

HRID 658118Notes

Reaction equation

HRID 658118 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)=[O:24])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([OH:22])[CH2:20][OH:21])[CH:14]=1)=[O:12].[C:32](N1C=CN=C1)(N1C=CN=C1)=[O:33]>>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]2[CH2:20][O:21][C:32](=[O:33])[O:22]2)[CH:14]=1)=[O:12])[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)=[O:24]

Participants

3

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178520867HCID 178520867, compound

Product 1

HCID 178519095HCID 178519095, compoundYield 9%

Conditions

Temperature
80 °C

Procedure

A 300 mg portion of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-[3-(1,2-dihydroxyethyl)phenyl]-3-(3-fluorophenyl)propane-1,3-dione and 200 mg of 1,1′-carbonyldiimidazole were dissolved in 7 ml of Tol and stirred at 80° C. for 12 hours. After concentration of the reaction liquid, the thus formed residue was purified by a silica gel column chromatography to obtain 30 mg (9%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-[3-(2-oxo-1,3-dioxolan-4-yl)phenyl]propane-1,3-dione as a yellow solid from a chloroform-methanol (10:1) eluate. ES+: 445

Workup

  1. customAfter concentration of the reaction liquid
  2. customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-34a9f90d34174f74a2e89e6310abc0f3
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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