Carbon Disulfide → HCID 178526474, compound

HRID 1780676Notes

Reaction equation

HRID 1780676 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[OH-].[K+].[C:14](=S)=[S:15]>C(O)C>[SH:15][C:14]1[O:11][C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 178526474HCID 178526474, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 mg portion of 2-amino-5-nitrophenol dissolved in 35 ml of ethanol was mixed with 180 mg of potassium hydroxide. After 10 minutes of reaction, the resulting solution was mixed with 35 ml of carbon disulfide and refluxed under heating for 48 hours. The reaction mixture was concentrated under a reduced pressure, and the resulting residue was dissolved in 300 ml of ethyl acetate and washed with an aqueous acidic solution of hydrochloric acid (pH 4) and water in that order. The resulting ethyl acetate layers were combined, dehydrated with sodium sulfate and then concentrated under a reduced pressure. Thereafter, the resulting residue was purified by a silica gel column chromatography (chloroform) to obtain 629 mg of 2-mercapto-6-nitrobenzoxazole.

Workup

  1. customAfter 10 minutes of reaction
  2. temperaturerefluxed
  3. temperatureunder heating for 48 hours
  4. concentrationThe reaction mixture was concentrated under a reduced pressure
  5. dissolutionthe resulting residue was dissolved in 300 ml of ethyl acetate
  6. washwashed with an aqueous acidic solution of hydrochloric acid (pH 4) and water in that order
  7. concentrationconcentrated under a reduced pressure
  8. customThereafter, the resulting residue was purified by a silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-4c2b3d2431b644668f312179b9e07627
Source dataset
uspto-grants-1997_05
Patent number
US05631257

Reaction notes

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