Ammonium Chloride → HCID 21834217, compound

HRID 1708993Notes

Reaction equation

HRID 1708993 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([C:10]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[O:11])[C:6]=2[CH:19]=1.[Mg].[Cl-].[NH4+]>CO.BrCCBr>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH:7]([C:10]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[O:11])[C:6]=2[CH:19]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 57199523HCID 57199523, compound

Product 1

HCID 21834217HCID 21834217, compound

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 887MethanolSolvent

Procedure

30 g of 5-amino-N,N-dipropyl-3-benzothiophencarboxamide were dissolved in 250 ml of dry methanol. 15 g of magnesium turnings were added (eventually activated by addition of a few drops of 1,2-dibromoethane). The mixture was stirred at 30°-35° C. for 4 hours with periodically cooling to keep the temperature down. 2 l of a saturated ammonium chloride solution were added and the product extracted with ethyl acetate. The organic phase was separated, washed with water, dried (MgSO4) and the solvent evaporated. Isopropyl ether was added, and by cooling the title compound precipitated and was filtered off. Yield: 20 g. M.P. 100° C.

Workup

  1. temperaturewith periodically cooling
  2. extractionthe product extracted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. additionIsopropyl ether was added
  8. temperatureby cooling the title compound
  9. customprecipitated
  10. filtrationwas filtered off

Sources & evidence

ORD record
ord-ccb9a07819024a9da4b14ac0ed3a3d7f
Source dataset
uspto-grants-1990_08
Patent number
US04946863

Reaction notes

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