Dimethylformamide → HCID 70353712, compound

HRID 2309380Notes

Reaction equation

HRID 2309380 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8]([N:10]1[C:18]2[C:13](=[CH:14][C:15]3[O:22][CH2:21][CH:20]=[CH:19][C:16]=3[CH:17]=2)[CH2:12][C:11]1=[O:23])[CH3:9].[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>ClCCl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([CH:12]2[C:13]3[C:18](=[CH:17][C:16]4[CH:19]=[CH:20][CH2:21][O:22][C:15]=4[CH:14]=3)[N:10]([CH2:8][CH3:9])[C:11]2=[O:23])=[O:33])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 709554-Fluorophenyl isocyanateHCID 70353795HCID 70353795, compound

Product 1

HCID 70353712HCID 70353712, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 128 mg. (3.2 mmoles) of sodium hydride (washed with petroleum ether) in 4 ml. of dimethylformamide was added 500 mg. (2.3 mmoles) of 1-ethyl-2-oxo-2,3-dihydro-pyrano[2,3-f]indole followed after 15 minutes of stirring by 0.36 ml. (3.2 mmoles) of 4-fluorophenylisocyanate. The reaction mixture was allowed to stir at room temperature for 30 minutes, and was then added to a mixture of dichloromethane (50 ml.) and ice water (50 ml.). The aqueous layer was extracted with 35 ml. of dichloromethane and was then acidified with 4N hydrochloric acid. The acidified layer was extracted with fresh dichloromethane, and the organic phase separated, dried over magnesium sulfate and concentrated under vacuum to dryness, 1.6 g. The residue was taken up in ethyl acetate, washed with a brine solution and dried over magnesium sulfate. Removal of the solvent gave 709 mg. of crude product. Recrystallization from dichloromethane-diisopropyl ether gave 490 mg. (60% yield) of product, m.p. 212°-214° C.

Workup

  1. stirringto stir at room temperature for 30 minutes
  2. extractionThe aqueous layer was extracted with 35 ml
  3. extractionThe acidified layer was extracted with fresh dichloromethane
  4. customthe organic phase separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum to dryness, 1.6 g
  7. washwashed with a brine solution
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of the solvent
  10. customgave 709 mg
  11. customRecrystallization from dichloromethane-diisopropyl ether
  12. customgave 490 mg

Sources & evidence

ORD record
ord-e9fc13ef9fb14a78ad0a7f9f5bcbcf3c
Source dataset
uspto-grants-1987_09
Patent number
US04695571

Reaction notes

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