Hydrochloric Acid → HCID 58007344, compound

HRID 1951918Notes

Reaction equation

HRID 1951918 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][S:13](=[O:24])(=[O:23])[N:12]=2)=[CH:7][CH:6]=1.Cl>C1(C)C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]2([CH3:1])[C:11]([C:8]3[CH:7]=[CH:6][C:5]([Cl:4])=[CH:10][CH:9]=3)=[N:12][S:13](=[O:24])(=[O:23])[NH:14]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59595063HCID 59595063, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58007344HCID 58007344, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl magnesium bromide (0.89 M tetrahydrofuran solution, 43.1 ml) was added dropwise to a toluene (200 ml) suspension of the compound (10.0 g, 29.5 mmol) obtained in Step 1 above at 0° C. The resulting mixture was stirred at room temperature for 1 hour and then 1 N aqueous hydrochloric acid solution was added, followed by extraction with ethyl acetate. Then, the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (11.1 g, quantitative) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThen, the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7b1961afbb3f4485a193aa1502272994
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

Loading…