Hydrochloric Acid → HCID 53348247, compound

HRID 1028414Notes

Reaction equation

HRID 1028414 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[C:10]([C:18]#[C:19][Si](C)(C)C)[CH:9]=1)(=[O:5])=[O:4].[OH-].[K+].Cl.CCCCCCC>C(O)C.O>[C:18]([C:10]1[CH:9]=[C:8]([CH2:7][CH2:6][S:3](=[O:5])(=[O:4])[NH:2][CH3:1])[CH:13]=[CH:12][C:11]=1[NH:14][C:15](=[O:17])[CH3:16])#[CH:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8900HeptaneHCID 14797Potassium HydroxideHCID 66973773HCID 66973773, compound

Product 1

HCID 53348247HCID 53348247, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
17.5 °C

Procedure

N-[4-(2-methylsulfamoyl-ethyl)-2-trimethylsilanylethynyl-phenyl]-acetamide (100 g) was dissolved in ethanol (1000 ml) at 25° C. and cooled to 15-20° C. Potassium hydroxide (20 gm) was added slowly maintaining temperature below 25° C., stirred for 2-3 hours and cooled to 10-15° C. pH of the reaction mixture was adjusted to 5 with 10% dilute HCl and concentrated under vacuum below 40° C. to obtain a residue. The residue was dissolved in water (250 ml) and extracted with dichloromethane (2000 ml). The organic layer was washed with water and concentrated under vacuum to obtain a residue. The residue was treated with heptane (200 ml) to obtain a solid which was filtered and dried under vacuum at 50-55° C. for 12 hours. (Yield: 70 g, HPLC Purity: 99%)

Workup

  1. temperaturemaintaining temperature below 25° C.
  2. temperaturecooled to 10-15° C. pH of the reaction mixture
  3. concentrationconcentrated under vacuum below 40° C.
  4. customto obtain a residue
  5. extractionextracted with dichloromethane (2000 ml)
  6. washThe organic layer was washed with water
  7. concentrationconcentrated under vacuum
  8. customto obtain a residue
  9. customto obtain a solid which
  10. filtrationwas filtered
  11. customdried under vacuum at 50-55° C. for 12 hours

Sources & evidence

ORD record
ord-1dcf2b84f10844ac9a488c430f0a6f22
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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