1,1'-Carbonyldiimidazole → HCID 10199947, compound

HRID 558261Notes

Reaction equation

HRID 558261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[O:5][C:6]1[C:7]([CH2:18][CH3:19])=[N:8][N:9]([CH2:13][C:14]([NH:16][NH2:17])=[O:15])[C:10]=1[CH2:11][CH3:12].[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[O:5][C:6]1[C:7]([CH2:18][CH3:19])=[N:8][N:9]([CH2:13][C:14]2[O:15][C:24](=[O:25])[NH:17][N:16]=2)[C:10]=1[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 10291828HCID 10291828, compound

Product 1

HCID 10199947HCID 10199947, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of the hydrazide (275 mg, 0.77 mmol) of Example 11 and 1,1′-carbonyl diimidazole 187 mg, 1.16 mmol) in dioxane (50 ml) was heated under reflux for 18 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (50 ml) and washed with water (25 ml). The organic layer was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume) to afford the title compound (112 mg) as a white solid m.p. 138-142° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane (50 ml)
  5. washwashed with water (25 ml)
  6. dry with materialThe organic layer was dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume)

Sources & evidence

ORD record
ord-82f6c3c5c2ca4a96a7637295ea8506bd
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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