Thiophenol → HCID 86739140, compound

HRID 904711Notes

Reaction equation

HRID 904711 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

Procedure

Sodium nitrite (0.18 g) is added at 0°-5° to a stirred suspension of 5-amino-2,3-dimethoxy-1,4-naphthoquinone (233 mg, 1 mmol) in 0.6 N hydrochloric acid (10 ml) and tetrahydrofuran (1 ml). The mixture is stirred at 5° for 10 minutes until a clear solution is obtained and is then neutralized by the addition of sodium carbonate. The ice cold solution is then slowly added to a vigorously stirred two-phase mixture in a nitrogen atmosphere at 50° 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 is partitioned between ethyl acetate (40 ml) and brine (100 ml). The ethyl acetate phase is dried over MgSO4 and concentrated in vacuo. The residue is 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, affords 70 mg of 2,3-dimethoxy-5-phenylthio-1,4-naphthoquinone, mp 76°-77°.

Workup

  1. customis obtained
  2. customAfter a total reaction time of 20 min, the mixture is partitioned between ethyl acetate (40 ml) and brine (100 ml)
  3. dry with materialThe ethyl acetate phase is dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is 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-707fa44dc8dc45ca85472d220996d16d
Source dataset
uspto-grants-1983_12
Patent number
US04419368

Reaction notes

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