Sodium Thiosulfate → HCID 68673705, compound

HRID 1927649Notes

Reaction equation

HRID 1927649 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH2:13][CH:14]([OH:21])[CH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])=[O:11])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14](=[O:21])[CH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68674059HCID 68674059, compound

Product 1

HCID 68673705HCID 68673705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propionamide (71.9 g, 202 mmol) in methylene chloride (1 L) was added Dess-Martin periodinane (100 g, 226 mmol). After 1.5 h, saturated sodium bicarbonate (500 mL) and saturated sodium thiosulfate (500 mL) were added and the mixture was stirred for another 10 minutes. The organic layer was separated and treated with another batch of saturated sodium bicarbonate (500 mL) and saturated sodium thiosulfate (500 mL). The organic layer was separated, dried over sodium sulfate, and concentrated to provide 3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propionamide, which was used without further purification.

Workup

  1. customThe organic layer was separated
  2. additiontreated with another batch of saturated sodium bicarbonate (500 mL) and saturated sodium thiosulfate (500 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-865657b8bc98403ba3046ad676e0dbcd
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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