Carbon Disulfide → HCID 178477630, compound

HRID 1990874Notes

Reaction equation

HRID 1990874 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:13].[C:14](=S)=[S:15].[OH-].[K+]>C(O)C>[CH2:11]([S:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:13][C:14]([SH:15])=[N:1][C:2]=2[CH:7]=1)(=[O:10])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 6432182-Amino-4-(ethylsulphonyl)phenol

Product 1

HCID 178477630HCID 178477630, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-amino-5-ethylsulfonyl-2-hydroxybenzene (20.13 g, 100.0 mmol, 1.0 equiv) in ethanol (200 mL) were added carbon disulfide (190.0 g, 150 mL, 2494 mmol, 25.0 equiv) and potassium hydroxide (6.73 g, 120 mmol, 1.2 equiv) and the reaction mixture heated to reflux over night. The solvent was evaporated, the residue treated with 1 M hydrochloric acid, extracted with ethyl acetate (3×150 mL) and the combined organic fractions dried over MgSO4. Evaporation of the organic solvent gave the crude product which was recrystallized from ethyl acetate to yield the title compound as yellowish solid. MS (ISN): 242.4 [M−H]−.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux over night
  3. customThe solvent was evaporated
  4. additionthe residue treated with 1 M hydrochloric acid
  5. extractionextracted with ethyl acetate (3×150 mL)
  6. dry with materialthe combined organic fractions dried over MgSO4
  7. customEvaporation of the organic solvent
  8. customgave the crude product which
  9. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eb22c90495154ab49d3bfae4e7353040
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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