Ethyl chloroformate → HCID 10179718, compound

HRID 2101740Notes

Reaction equation

HRID 2101740 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[CH:11]=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[Li]CCCC.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1COCC1.CCCCCC>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:9]1[N:10]=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:12]([CH3:13])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 22066095HCID 22066095, compoundHCID 178418339Butyllithium

Product 1

HCID 10179718HCID 10179718, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1.1 g (3.25 mmol) of 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-imidazole in 30 mL of dry THF was cooled in a −78° C. bath and 1.7 mL of 2.5 M n-BuLi in hexane was dropwise added. After stirring the solution for 1 h it was added with a canula to 0.623 mL of ethyl chloroformate in THF cooled in a −78° C. bath. The cold bath was removed and the reaction was stirred for 1 h then quenched with water. The mixture was extracted with EtOAc. The EtOAc layer was washed with brine, dried and concentrated. The residue was chromatographed using a gradient of 10-20% EtOAc-hexane to isolate the desired product.

Workup

  1. customThe cold bath was removed
  2. stirringthe reaction was stirred for 1 h
  3. customthen quenched with water
  4. extractionThe mixture was extracted with EtOAc
  5. washThe EtOAc layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed

Sources & evidence

ORD record
ord-9134e2b52c0f468f84df80e8ea7b3e6d
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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