Lithium iodide → HCID 20135083, compound

HRID 580408Notes

Reaction equation

HRID 580408 reaction equation
[I-].[Li+].COC([C:7]1([CH2:31][CH:32]=[CH2:33])[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][C:11]2[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=[CH:25][C:10]=2[NH:9][C:8]1=[O:30])=O>N1C=CC=CC=1.O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:13]1[CH2:12][C:11]2[C:22]([C:26]([F:27])([F:28])[F:29])=[CH:23][CH:24]=[CH:25][C:10]=2[NH:9][C:8](=[O:30])[CH:7]1[CH2:31][CH:32]=[CH2:33]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 20135070HCID 20135070, compound

Product 1

HCID 20135083HCID 20135083, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 1049PyridineSolvent2×

Procedure

Lithium iodide (11.98 g; 89.44 mmole) was added to 1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-3-(2-propenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (9.69 g; 22.36 mmole) in pyridine (40 ml) and water (a few drops). The mixture was refluxed with stirring for 11 hours. The pyridine was vacuum distilled off and the residue was dissolved into methanol and washed with 1N hydrochloric acid (three times), and saturated sodium chloride, and dried (magnesium sulfate). The concentrated residue was black indicating some decomposition occurred. The 9.67 g of this black residue was flash chromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 1:1-hexane/ethyl acetate). Appropriate fractions were combined and concentrated giving 5.87 g of the title compound as a solid.

Workup

  1. temperatureThe mixture was refluxed
  2. distillationdistilled off
  3. dissolutionthe residue was dissolved into methanol
  4. washwashed with 1N hydrochloric acid (three times), and saturated sodium chloride
  5. dry with materialdried (magnesium sulfate)
  6. customchromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 1:1-hexane/ethyl acetate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-23cc770041854ba6ae44e2db714a5176
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

Loading…