Hydrochloric Acid → HCID 178526153, compound

HRID 1090264Notes

Reaction equation

HRID 1090264 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13]CC)=[S:12])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[Si](C)(C)[O-].[K+].C(OCC)(=O)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[S:12])=[C:5]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23668039Potassium trimethylsilanolateHCID 86745392Ethyl 5-chloro-3-phenylthioindole-2-carboxylate

Product 1

HCID 178526153HCID 178526153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 57 mg of ethyl 5-chloro-3-phenylthioindole -2-carboxylate from Preparation 5 in 1.7 mL of dry tetrahydrofuran, under argon, was added 48 mg of solid potassium trimethylsilanolate. The resultant mixture was stirred at room temperature for 20 h. Ethyl acetate and 1N HCl were then added. The organic layer was washed with brine (2x) and dried over MgSO4. Filtration and concentration gave a yellow gum which was triturated with ether hexane to give the title compound.

Workup

  1. washThe organic layer was washed with brine (2x)
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration
  4. customgave a yellow gum which
  5. customwas triturated with ether hexane

Sources & evidence

ORD record
ord-194ee22c203d4c5ba46d23a1a6b8bf71
Source dataset
uspto-grants-1992_01
Patent number
US05081138

Reaction notes

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