Hydrochloric Acid → HCID 10358098, compound

HRID 648993Notes

Reaction equation

HRID 648993 reaction equation
[CH:1]([N-]C(C)C)(C)[CH3:2].[Li+].C(NC(C)C)(C)C.C([Li])CCC.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH2:32][N:31]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:30](=[O:41])[CH:29]=2)=[CH:24][CH:23]=1.C(I)C.Cl>O1CCCC1>[CH2:1]([C:29]1[C:30](=[O:41])[N:31]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[CH2:32][C:28]=1[C:25]1[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=1)[CH3:2]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 4399373HCID 4399373, compoundHCID 178418339Butyllithium

Product 1

HCID 10358098HCID 10358098, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium diisopropylamide is generated from diisopropylamine (122 mL, 0.87 mol) and n-butyllithium (2.5 M in hexane, 348 mL, 0.87 mol) in tetrahydrofuran (1.5 L) under a nitrogen atmosphere at -60° C., and 4-(4-fluorophenyl)-1,5-dihydro-1-(4-methoxyphenyl)-2H-pyrrol-2-one (235 g, 0.83 mol) is added to this mixture. The mixture is stirred for 30 minutes at -50° C., 1 hr at 0° C., and then re-cooled to -60° C. Ethyl iodide (73 mL, 0.91 mol) is added, and the reaction is allowed to warm slowly to 25° C., and stirred at this temperature for 18 hr. The mixture is poured into 1.5 L of 4 N HCl and stirred for 1 hr. The mixture is then extracted with methylene chloride, and the extracts are dried with magnesium sulfate and evaporated. Recrystallization of the residue from ethanol followed by drying under vacuum at 60° C. for 18 hr gives the title compound.

Workup

  1. temperaturere-cooled to -60° C
  2. temperatureto warm slowly to 25° C.
  3. stirringstirred at this temperature for 18 hr
  4. stirringstirred for 1 hr
  5. extractionThe mixture is then extracted with methylene chloride
  6. dry with materialthe extracts are dried with magnesium sulfate
  7. customevaporated
  8. customRecrystallization of the residue from ethanol
  9. customby drying under vacuum at 60° C. for 18 hr

Sources & evidence

ORD record
ord-cbb84db31cc14eb19b035dd5f385c1f5
Source dataset
uspto-grants-1988_04
Patent number
US04737511

Reaction notes

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