Sodium bis(trimethylsilyl)amide → HCID 54678918, compound

HRID 1781621Notes

Reaction equation

HRID 1781621 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[NH:6][C:7](=[O:19])[CH2:8][S:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:24][C:21]1[CH:20]=[C:5]2[C:4]([C:3]([OH:2])=[C:8]([S:9][CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7](=[O:19])[NH:6]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 22364792HCID 22364792, compound

Product 1

HCID 54678918HCID 54678918, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2 g (5.3 mmol) of 4-chloro-N-(3-phenylpropylthio)acetyl-anthranilic acid methyl ester are placed in 20 ml of tetrahydrofuran at 0°. A 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide is added dropwise thereto. The mixture is then stirred for 20 minutes at 0° and for 2 hours at room temperature. The reaction mixture is poured into 200 ml of 2N hydrochloric acid/ice and the resulting white suspension is filtered off. The resulting colourless crystals are made into a suspension in ethanol and stirred for 2 hours. The mixture is filtered, followed by washing with ethanol and diethyl ether. After drying, 7-chloro-4-hydroxy-3-(3-phenylpropylthio)-2(1H)-quinolone is obtained in the form of colourless crystals having a melting point of 184°-186°.

Workup

  1. filtrationthe resulting white suspension is filtered off
  2. stirringstirred for 2 hours
  3. filtrationThe mixture is filtered
  4. washby washing with ethanol and diethyl ether
  5. customAfter drying

Sources & evidence

ORD record
ord-553c1de6521b4135bb3b5f05a2676673
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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