1,1'-Carbonyldiimidazole → HCID 69319664, compound

HRID 748633Notes

Reaction equation

HRID 748633 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)[O:5][CH:6]1[CH2:10][NH:9][CH:8]([CH2:11][OH:12])[CH2:7]1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)[O:5][CH:6]1[CH2:10][N:9]2[C:19](=[O:20])[O:12][CH2:11][CH:8]2[CH2:7]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57433451HCID 57433451, compound

Product 1

HCID 69319664HCID 69319664, compoundYield 128.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.29 g of [4-(3-fluoro-5-nitro-phenoxy)-pyrrolidin-2-yl]-methanol in 20 mL of anhydrous dichloromethane was added in one portion 0.82 g of 1,1′-carbonyldiimidazole and the resultant mixture stirred at room temperature under N2 for 3 hours. The reaction mixture was diluted with 30 mL of dichloromethane and washed with H2O (2×25 mL) and brine (25 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to give 1.82 g of a light yellow solid. Purification over silica gel resulted in 0.825 g of 6-(3-Fluoro-5-nitro-phenoxy)-tetrahydro-pyrrolo[1,2-c]oxazol-3-one as a white solid.

Workup

  1. washwashed with H2O (2×25 mL) and brine (25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9a078a67ad1045888f38f1bf07b0f8b5
Source dataset
uspto-grants-2008_07
Patent number
US07399866B2

Reaction notes

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