HCID 10956231, compound → HCID 53857488, compound

HRID 1106700Notes

Reaction equation

HRID 1106700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([S:12][CH3:13])=[N:10][OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C)([O-])C.[K+].[Cl:20][C:21]1[N:22]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:34]Cl)[C:23](=[O:27])[N:24]([CH3:26])[N:25]=1>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([S:12][CH3:13])=[N:10][O:11][CH2:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:22]2[C:23](=[O:27])[N:24]([CH3:26])[N:25]=[C:21]2[Cl:20])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 10956231HCID 10956231, compoundHCID 23665647Potassium tert-butoxideHCID 131721786HCID 131721786, compound

Product 1

HCID 53857488HCID 53857488, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Step C (2.07 g) was dissolved in 10 mL of tetrahydrofuran and 10 mL of 1.0 M potassium t-butoxide in THF was added dropwise. After the addition was complete, the mixture was stirred 15 min, and then the title compound of Step E (2.06 g) was added. The reaction mixture was stirred at room temperature overnight, and then diluted with 20 mL of water and extracted with three 30 mL portions of ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated to give 3.53 g of the title compound of Step F as an oil. 1H NMR (CDCl3): δ 7.5 (m,5H), 7.25 (m,2H), 5.34 (d,1H), 5.18 (d,1H), 3.49 (s,3H), 2.08 (s,3H). The crude product contained minor amounts of impurities and solvent, but the material was not further purified before Step G.

Workup

  1. additionAfter the addition
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. extractionextracted with three 30 mL portions of ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f27fe34a26874a9e84fb928a576864a4
Source dataset
uspto-grants-2000_05
Patent number
US06057352

Reaction notes

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