1,1'-Carbonyldiimidazole → HCID 22049200, compound

HRID 2087152Notes

Reaction equation

HRID 2087152 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([NH2:14])[C:10]([CH3:13])([OH:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]([CH3:11])([CH3:13])[O:12][C:15](=[O:16])[NH:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18623229(+)-β-Amino-3,4-difluoro-α,α-dimethylbenzeneethanol

Product 1

HCID 22049200HCID 22049200, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3,4-difluorophenyl)-2-methyl-2-hydroxypropylamine (3.00 g, 14.9 mmol) and carbonyldiimidazole (2.418 g, 14.9 mmol) in dichloromethane (150 mL) was heated at reflux temperature for 36 h and the solvent evaporated. The residue was purified by column chromatography on silica gel using chloroform/ethyl acetate (9:1) to give the product as a viscous oil which solidified on standing (1.80 g, 50% yield). The product was used in the next step without further characterization.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 36 h
  3. customthe solvent evaporated
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e205b33a2a0441808202861a13ca01ff
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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