Thiophenol → HCID 86739140, compound

HRID 358362Notes

Reaction equation

HRID 358362 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8](=O)[C:9](OC)=[C:10](OC)[C:11]2=O.[C:22](=[O:25])([O-])[O-].[Na+].[Na+].[OH-:28].[K+].[C:30]1([SH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[O:37]1[CH2:41]CCC1>Cl.C(OCC)(=O)C.O>[CH3:41][O:37][C:31]1[C:30](=[S:36])[C:35]2[C:34]([C:33](=[O:28])[C:32]=1[O:25][CH3:22])=[C:8]([C:7]1[CH:6]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:9]=[CH:10][CH:11]=2

Participants

10

Reactant 6

HCID 7969ThiophenolHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 122506961,4-Naphthalenedione, 5-amino-2,3-dimethoxy-HCID 23668193Sodium Nitrite

Product 1

HCID 86739140HCID 86739140, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Sodium nitrite (0.18 g) was added at 0°-5° C. to a stirred suspension of 5-amino-2,3-dimethoxy-1,4-naphthoquinone (233 mg, 1 mmol) in 0.6N hydrochloric acid (10 ml) and tetrahydrofuran (1 ml). The mixture was stirred at 5° C. for 10 minutes until a clear solution was obtained and was then neutralized by the addition of sodium carbonate. The ice cold solution was then slowly added to a vigorously stirred two-phase mixture in a nitrogen atmosphere at 50° C. composed of potassium hydroxide (0.16 g), water (10 ml), thiophenol (0.32 ml) and ethyl acetate (35 ml). After a total reaction time of 20 min, the mixture was partitioned between ethyl acetate (40 ml) and brine (100 ml). The ethyl acetate phase was dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography on a thick layer silica gel plate using acetone:toluene:chloroform (1:20:20) giving a solid that, after recrystallizing from isopropanol, afforded 70 mg of 2,3-dimethoxy-5-phenylthio-1,4-naphthoquinone, mp 76°-77° C.

Workup

  1. customwas obtained
  2. customAfter a total reaction time of 20 min, the mixture was partitioned between ethyl acetate (40 ml) and brine (100 ml)
  3. dry with materialThe ethyl acetate phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on a thick layer silica gel plate
  6. customgiving a solid that,
  7. customafter recrystallizing from isopropanol

Sources & evidence

ORD record
ord-c61e5b14ff7d4e70bd209cb687905634
Source dataset
uspto-grants-1984_08
Patent number
US04466981

Reaction notes

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