Water → 7,9-Dimethoxy-5-oxa-11-thia-benzo[b]fluoren-10-one

HRID 411661Notes

Reaction equation

HRID 411661 reaction equation
[C:1]([O:10][CH3:11])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[H-].[Na+].Cl[CH2:15][C:16]([C:18]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20]C=1F)=[O:17].O>CN(C=O)C>[CH3:27][O:26][C:21]1[CH:22]=[C:23]([O:24][CH3:25])[C:18]2[C:16](=[O:17])[C:15]3[S:4][C:3]4[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=4[C:1]=3[O:10][C:11]=2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 24758Sodium hydride2×HCID 185413192-Chloro-1-(2-fluoro-4,6-dimethoxyphenyl)ethan-1-one

Product 1

HCID 101932297,9-Dimethoxy-5-oxa-11-thia-benzo[b]fluoren-10-oneYield 40.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution consisting of methyl thiosalicylate 28 (0.67 g, 4.0 mmol) in DMF was treated with NaH (0.19 g, 4.8 mmol as a 60% dispersion in mineral oil) and stirred at rt for approximately 5-10 minutes and then Example 27 (1 g, 4.3 mmol) was added followed by additional NaH (0.4 g, 10 mmol, as a 60% dispersion in mineral oil) and the reaction was heated at 100° C. for 30 minutes. The crude reaction mixture was poured into water, filtered, and the solid product washed with additional water, MeOH and hexanes. The product thus obtained was triturated with MeOH to yield 29 (0.51 g): 1H NMR (DMSO-d6) δ 8.16 (d, 2H, J=2.3 Hz), 7.71-7.61 (m, 2H), 6.91 (d, 1H, J=2.3 Hz), 6.63 (d, 1H, J=2.3 Hz), 3.95 (s, 3H), 3.89 (s, 3H); MS 335 (M+Na)+.

Workup

  1. temperatureas a 60% dispersion in mineral oil) and the reaction was heated at 100° C. for 30 minutes
  2. customThe crude reaction mixture
  3. filtrationfiltered
  4. washthe solid product washed with additional water, MeOH and hexanes
  5. customThe product thus obtained
  6. customwas triturated with MeOH

Sources & evidence

ORD record
ord-5bcf4f84039446e4adb730b970aeceb7
Source dataset
uspto-grants-2003_05
Patent number
US06559177B2

Reaction notes

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