Carbon Disulfide → HCID 178488033, compound

HRID 1780673Notes

Reaction equation

HRID 1780673 reaction equation
Cl.[OH:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[OH-].[K+].[C:14](=S)=[S:15]>C(O)C>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:4]2[N:5]=[C:14]([SH:15])[O:2][C:3]=2[CH:9]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 122101842-Amino-5-methoxyphenol Hydrochloride

Product 1

HCID 178488033HCID 178488033, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50 mg portion of 2-hydroxy-4-methoxyaniline hydrochloride dissolved in 15 ml of ethanol was mixed with 16 mg of potassium hydroxide. After 10 minutes of reaction, to this was added 50 ml of carbon disulfide to carry out 24 hours of heating under reflux. The reaction mixture was concentrated under a reduced pressure, and the resulting residue was dissolved in 100 ml of dichloromethane, washed with water, dehydrated with magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (dichloromethane:methanol=30:1) to obtain 46 mg of 6-methoxy-2-mercaptobenzoxazole.

Workup

  1. customAfter 10 minutes of reaction
  2. temperatureof heating
  3. temperatureunder reflux
  4. concentrationThe reaction mixture was concentrated under a reduced pressure
  5. dissolutionthe resulting residue was dissolved in 100 ml of dichloromethane
  6. washwashed with water
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified by a silica gel column chromatography (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-27dc36527670462f9eae30710e17ab29
Source dataset
uspto-grants-1997_05
Patent number
US05631257

Reaction notes

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