1,1'-Carbonyldiimidazole → HCID 60052185, compound

HRID 494991Notes

Reaction equation

HRID 494991 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[C:7]([O:15][CH3:16])=[CH:6][C:5]=1[OH:17])[CH3:2].[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19]>O1CCCC1>[CH2:1]([N:3]1[C:4]2[CH:9]=[C:8]([CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[C:7]([O:15][CH3:16])=[CH:6][C:5]=2[O:17][C:18]1=[O:19])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57682934HCID 57682934, compound

Product 1

HCID 60052185HCID 60052185, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

80 mg of 2-ethylamino-5-methoxy-4-(3-methyl-2-butenyl)phenol was dissolved in 5 ml of tetrahydrofuran under nitrogen atmosphere. Then, 0.11 g of 1,1′-carbonyldiimidazole was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, the mixture was further stirred at 50° C. for 1 hour. The reaction solution was concentrated under a reduced pressure. The residue was diluted with ethyl acetate and then washed with a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 60 mg of the subject compound.

Workup

  1. stirringThereafter, the mixture was further stirred at 50° C. for 1 hour
  2. concentrationThe reaction solution was concentrated under a reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with a saturated sodium chloride aqueous solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9744f641d2554702ac01ebed705104da
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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