Hydrochloric Acid → HCID 178446180, compound

HRID 2393606Notes

Reaction equation

HRID 2393606 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1([CH2:23][CH2:24][C:25]#[N:26])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6].C([Sn]([N:44]=[N+:45]=[N-:46])(CCCC)CCCC)CCC.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1([CH2:23][CH2:24][C:25]2[NH:46][N:45]=[N:44][N:26]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 18976205HCID 18976205, compound

Product 1

HCID 178446180HCID 178446180, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2.00 g of 3,4-dichloro-N-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]benzamide, 3.0 g of tributyltin azide (Bu3SnN3) and 1.5 ml of toluene was stirred at 110° C. for 3 hours. After cooling, a 50 ml of ethanolic 6.4% hydrochloric acid solution was added to the mixture, and the resulting mixture was stirred at room temperature for 30 minutes. After removal of solvent by evaporation, ethyl acetate and then an aqueous saturated potassium fluoride solution were added to the residue, and insolubles were removed by filtration. The ethyl acetate layer was collected by separation, washed with water and evaporated. The residue was dissolved in an aqueous 5% sodium hydroxide solution and washed with water with diethyl ether. After the aqueous layer was made acidic with 10% hydrochloric acid, it was extracted with ethyl acetate. The extract was washed with water and dried, and solvent was evaporated. The residue was recrystallized from ethyl acetate to afford 1.72 g of 3,4-dichloro-N-{2,3-dihydro-2-oxo-1-pentyl-3-[2-(1H-tetrazol-5-yl)ethyl]-1H-indol-3-yl}-benzamide as colorless needles. Melting point: 142° TO 147° C., IR (Nujol) (cm-1): 3340, 1705, 1655, 1675, 1615, FAB-MS (m/z): 489 & 487 (MH+).

Workup

  1. temperatureAfter cooling
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. customAfter removal of solvent
  4. customby evaporation, ethyl acetate
  5. additionan aqueous saturated potassium fluoride solution were added to the residue, and insolubles
  6. customwere removed by filtration
  7. customThe ethyl acetate layer was collected by separation
  8. washwashed with water
  9. customevaporated
  10. dissolutionThe residue was dissolved in an aqueous 5% sodium hydroxide solution
  11. washwashed with water with diethyl ether
  12. extractionwas extracted with ethyl acetate
  13. washThe extract was washed with water
  14. customdried
  15. customsolvent was evaporated
  16. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2ff0c650dd00439f9012eabe142f5220
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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