1,1'-Carbonyldiimidazole → HCID 10199947, compound

HRID 2114625Notes

Reaction equation

HRID 2114625 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-59148bdbd3594c0fb585b724a58c416c
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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