Carbon Disulfide → HCID 178515778, compound

HRID 2399849Notes

Reaction equation

HRID 2399849 reaction equation
[C:1](=[S:3])=S.[OH-].[K+].[N+:6]([C:9]1[CH:10]=[C:11](O)[C:12]([OH:15])=[CH:13][CH:14]=1)([O-])=O.S(S([O-])=O)([O-])=[O:18].[Na+].[Na+]>O.CO>[OH:15][C:12]1[CH:11]=[CH:10][C:9]2[N:6]=[C:1]([SH:3])[O:18][C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 6348Carbon Disulfide2×HCID 14797Potassium Hydroxide2×HCID 24489Sodium DithioniteHCID 35051094-Nitrocatechol

Product 1

HCID 178515778HCID 178515778, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

Carbon disulphide (0.9 ml, 15 mmol) was added to a solution of potassium hydroxide (0.65 g, 11 mmol) in a mixture of water (1 ml) and methanol (10 ml), followed by 4-nitro 1,2-benzenediol (1.5 g, 10 mmol). To this mixture was added dropwise a solution of sodium dithionite (6,5 g, 30 mmol) and potassium hydroxide (3.9 g, 70 mmol) in water (50 ml); strong heat evolution was observed. After 10 minutes, carbon disulphide (0.9 ml, 15 mmol) was added and the mixture heated to 75° C. for 3 hours. The mixture was then cooled in an ice bath and the precipitate filtered off. The filtrate was acidified to approximately pH3 with concentrated hydrochloric acid and the yellow precipitate was collected, washed with water and air dried. The yield was 1.05 g (65%).

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. filtrationthe precipitate filtered off
  3. customthe yellow precipitate was collected
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-a8ba1cefa5db41ba95b749562c62f658
Source dataset
uspto-grants-1995_09
Patent number
US05451681

Reaction notes

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