Hydrochloric Acid → HCID 67095051, compound

HRID 1618756Notes

Reaction equation

HRID 1618756 reaction equation
C([N:4]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Br:20])[CH:18]=2)[C:6]2([CH2:11][CH2:10][S:9](=[O:13])(=[O:12])[CH2:8][CH2:7]2)[CH2:5]1)(=O)C.Cl>CO>[Br:20][C:17]1[CH:18]=[C:19]2[NH:4][CH2:5][C:6]3([CH2:11][CH2:10][S:9](=[O:13])(=[O:12])[CH2:8][CH2:7]3)[C:14]2=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58221585HCID 58221585, compound

Product 1

HCID 67095051HCID 67095051, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-acetyl-6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide (0.75 g, 2.1 mmol) and 5 N HCl (8 mL) in MeOH (20 mL) was heated at reflux for 3 h. After this time the solvent was removed in vacuo to give 6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide as an off-white solid. Purification by column chromatography gave 6-Bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide. Mass Spectrum (ESI) m/e=316.0 [(M+1) (79Br)] and 318.0 [(M+1) (81Br)]

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customAfter this time the solvent was removed in vacuo

Sources & evidence

ORD record
ord-13c63594b9fc4b03a758204608a46a4d
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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