Triethylamine → HCID 10180140, compound

HRID 1060866Notes

Reaction equation

HRID 1060866 reaction equation
[F:1][C:2]([F:26])([F:25])[CH:3]([C:5]1[C:14]2[C:9](=[C:10]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([CH3:24])[CH:6]=1)[OH:4].[CH3:27][N:28]=[C:29]=[O:30].C(N(CC)CC)C>ClCCl>[F:26][C:2]([F:1])([F:25])[CH:3]([O:4][C:29](=[O:30])[NH:28][CH3:27])[C:5]1[C:14]2[C:9](=[C:10]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([CH3:24])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 12970215HCID 12970215, compound

Product 1

HCID 10180140HCID 10180140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,2,2-trifluoro-1-[2-methyl-8-(2,4,6-trimethyl-phenyl)quinolin-4-yl]-ethanol (50 mg), methyl isocyanate (0.5 ml), triethylamine (0.1 ml) in dichloromethane (2 ml) was heated at reflux for 2 hrs. The mixture was quenched with water and extracted with chloroform. The organic layer was separated, dried and concentrated to give the crude material which was purified by silica gel column chromatography using chloroform as eluent to give the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hrs
  3. customThe mixture was quenched with water
  4. extractionextracted with chloroform
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customto give the crude material which
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-86d2832a0d484d5c9ca93931c3c55fd1
Source dataset
uspto-grants-2003_02
Patent number
US06525067B1

Reaction notes

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