Sodium Hydroxide → HCID 59488865, compound

HRID 1960166Notes

Reaction equation

HRID 1960166 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[S:27])[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[K]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]2[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=3)[S:27][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5462222PotassiumHCID 59488854HCID 59488854, compound

Product 1

HCID 59488865HCID 59488865, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

N-(4-Benzyloxy-phenyl)-4-chloro-3-nitro-thiobenzamide (2 g, 5 mmol) was dissolved in methanol (100 ml). Sodium hydroxide (1.6 g in 5 ml water) was added followed by Triton B (2.1 ml, 5 mmol, commercially available). The mixture was cooled in an ice-bath. Potassium ferri(III) cyanide (13.2 g in 50 ml water) was added drop wise with vigorous stirring. The reaction mixture was allowed to warm up overnight and was further warmed to 130° C. for 1 hour. The reaction mixture was cooled and extracted with ethyl acetate/water. The organic phase dried and the solvent removed under reduced pressure. The product, compound was purified by flash chromatography with Hexane/Ethyl acetate as eluent.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. temperatureto warm up overnight
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate/water
  5. customThe organic phase dried
  6. customthe solvent removed under reduced pressure
  7. customThe product, compound was purified by flash chromatography with Hexane/Ethyl acetate as eluent

Sources & evidence

ORD record
ord-8fea444fc3ff4ab7bf0b7153df67dc8c
Source dataset
uspto-grants-2013_04
Patent number
US08410312B2

Reaction notes

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