1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19919849, compound

HRID 1033124Notes

Reaction equation

HRID 1033124 reaction equation
[CH2:1]([N:5]1[CH:9](P(=O)(OCC)OCC)[C:8](=[O:18])[NH:7][C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].[Cl-].[Li+].C1CCN2C(=NCCC2)CC1.[CH2:33]([C:37]1[N:38]([CH2:44][C:45]2[CH:54]=[CH:53][C:48]([C:49]([O:51][CH3:52])=[O:50])=[CH:47][C:46]=2[Cl:55])[C:39]([CH:42]=O)=[CH:40][N:41]=1)[CH2:34][CH2:35][CH3:36]>C(#N)C>[CH2:33]([C:37]1[N:38]([CH2:44][C:45]2[CH:54]=[CH:53][C:48]([C:49]([O:51][CH3:52])=[O:50])=[CH:47][C:46]=2[Cl:55])[C:39](/[CH:42]=[C:9]2\[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6](=[O:19])[NH:7][C:8]\2=[O:18])=[CH:40][N:41]=1)[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 19919860HCID 19919860, compoundHCID 19919877Methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-3-chlorobenzoate

Product 1

HCID 19919849HCID 19919849, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of diethyl 3-butyl-2,5-dioxo-4-imidazolylphosphonate (0.49 g, 1.72 mmol) in acetonitrile (5 mL) was added lithium chloride (0.15 g, 3.47 mmol) and then DBU (0.52 mL, 3.47 mmol). This mixture was stirred for 5 minutes under N2. Methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-3-chlorobenzoate (0.48 g, 1.43 mmol) in acetonitrile (5 mL) was added and the mixture stirred for 4 days. The solvent was removed in vacuo and the isomers separated by chromatography eluting with (1-5)% methanol in chloroform.

Workup

  1. stirringthe mixture stirred for 4 days
  2. customThe solvent was removed in vacuo
  3. customthe isomers separated by chromatography
  4. washeluting with (1-5)% methanol in chloroform

Sources & evidence

ORD record
ord-ad07f7546db347708ae0b8c8021980a1
Source dataset
uspto-grants-1994_05
Patent number
US05308853

Reaction notes

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