Ammonium Chloride → HCID 58221585, compound

HRID 1618755Notes

Reaction equation

HRID 1618755 reaction equation
[C:1]([N:4]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[C:6]2([CH2:11][CH2:10]S[CH2:8][CH2:7]2)[CH2:5]1)(=[O:3])[CH3:2].O[O:20][S:21]([O-:23])=O.[K+].[NH4+].[Cl-]>CO.O.CC(C)=O>[C:1]([N:4]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[C:6]2([CH2:7][CH2:8][S:21](=[O:23])(=[O:20])[CH2:10][CH2:11]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 23707502Potassium hydroxy sulfiteHCID 58221582HCID 58221582, compound

Product 1

HCID 58221585HCID 58221585, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred ice-cooled suspension of crude 1-acetyl-6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran] (0.68 g, 2.1 mmol) in MeOH (40 mL), H2O (5 mL) and acetone (10 mL) was added oxone (2.58 g, 4.20 mmol) in H2O (15 mL). The resulting mixture was stirred at rt for 20 h. After this time the mixture was poured into ice and saturated aqueous NH4Cl and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo to give 1-acetyl-6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro-[indole-3,4′-thiopyran]1′,1′-dioxide as a white solid. Mass Spectrum (ESI) m/e=358.0 [(M+1) (79Br)] and 360.0 [(M+1) (81Br)].

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0977a6be6c341b9887aae88d896c80e
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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