Hydrochloric Acid → HCID 86670069, compound

HRID 1028415Notes

Reaction equation

HRID 1028415 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([C:22]#[C:23][Si](C)(C)C)[CH:9]=1)(=[O:5])=[O:4].[OH-].[K+].Cl.CCCCCCC>C(O)C.O>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([C:22]#[CH:23])[CH:9]=1)(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8900HeptaneHCID 14797Potassium HydroxideHCID 66973824HCID 66973824, compound

Product 1

HCID 86670069HCID 86670069, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
17.5 °C

Procedure

2-(4-benzylamino-3-trimethylsilanylethynyl-phenyl)-ethanesulfonic acid methylamide (100 g) was dissolved in ethanol (1000 ml) at 25° C. and cooled to 15-20° C. Potassium hydroxide (20 g) 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 (300 ml) and extracted with dichloromethane (2500 ml). The organic layer was washed with water and concentrated under vacuum to obtain a residue. The residue was treated with heptane (400 ml) to obtain a solid which was filtered and dried under vacuum at 50-55° C. for 12 hours. (Yield: 75 g, HPLC Purity: 98%)

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 (2500 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-dbda437e022c4448a81dc852cee5f5b8
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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