Potassium Iodide → HCID 67280700, compound

HRID 1516324Notes

Reaction equation

HRID 1516324 reaction equation
N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C@H:7]([OH:19])[C@H:8]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:36].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[OH:19][C@H:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:2]([I:36])=[CH:3][CH:4]=2)[C@@H:8]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium NitriteHCID 67280848HCID 67280848, compound

Product 1

HCID 67280700HCID 67280700, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Cool a suspension of tert-butyl N-[(1S,2S)-6-amino-2-hydroxy-indan-1-yl]carbamate (25.0 g, 94.6 mmol) in acetonitrile (800 mL) in an ice bath for 30 min and add p-toluenesulfonic acid monohydrate (53.97 g, 283.7 mmol) in one portion. Add a solution of sodium nitrite (13.05 g, 189.2 mmol) in water (30 mL) to the mixture in portions for 5 min and stir for 30 min. Add a solution of potassium iodide (39.25 g, 236.5 mmol) in water (50 mL) dropwise to the mixture over 10 min. and stir for 20 min. in an ice bath. Allow the mixture to warm up to room temperature and stir for 1.5 hr. Make the dark red solution alkaline with 10% aqueous sodium carbonate. Concentrate the resulting mixture in vacuo to remove the acetonitrile. Collect the brown precipitate by filtration and dry in a vacuum oven at 50° C. overnight to obtain the title compound (33.9 g, 96%). LC-ES/MS m/z 320 [M+H]+.

Workup

  1. temperatureCool
  2. stirringstir for 20 min. in an ice bath
  3. stirringstir for 1.5 hr
  4. concentrationConcentrate the resulting mixture in vacuo
  5. customto remove the acetonitrile
  6. customCollect the brown precipitate
  7. filtrationby filtration
  8. customdry in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-b251690b56af49378b0b5d6f1495e717
Source dataset
uspto-grants-2012_07
Patent number
US08227468B2

Reaction notes

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