Hydroquinone → HCID 131727025, compound

HRID 30243Notes

Reaction equation

HRID 30243 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:13][CH:12]2[CH:8]([CH2:9][C:10]3[CH:16]=[C:15]([CH3:17])[S:14][C:11]=32)[CH2:7]1)=[O:5])[CH3:2].C1(C=CC(O)=CC=1)O.C1C(=O)N([Br:33])C(=O)C1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CC(O)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:13][CH:12]2[CH:8]([CH2:9][C:10]3[C:16]([Br:33])=[C:15]([CH3:17])[S:14][C:11]=32)[CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 59789449HCID 59789449, compound

Product 1

HCID 131727025HCID 131727025, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

The product of Example 15, step c) (69.1 mg, 0.30 mmol) was placed in a vial and diluted with CHCl3 (740 μl) and AcOH (740 μl). Next, hydroquinone (−5 mg) was added followed by NBS (51.4 mg, 0.31 mmol) and the contents were heated to 40° C. for 6 hours. The crude reaction mixture was carefully poured into saturated NaHCO3 (10 ml) and extracted with EtOAc (3×5 ml). The organic layer was dried (MgSO4) and purified by preparative TLC using hexanes/EtOAc 50:50 providing the subtitled product. MS calculated for C13H16BrNO2S+H 330, observed 330, 332.

Workup

  1. customThe crude reaction mixture
  2. extractionextracted with EtOAc (3×5 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. custompurified by preparative TLC

Sources & evidence

ORD record
ord-0bb720bc3a584a8088bc1b2dfc44470f
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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