Sodium bis(trimethylsilyl)amide → HCID 54735472, compound

HRID 1781633Notes

Reaction equation

HRID 1781633 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:20][C:21]([Cl:27])=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[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:27][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)=[C:23]([N+:24]([O-:26])=[O:25])[CH:22]=1

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 22364789HCID 22364789, compound

Product 1

HCID 54735472HCID 54735472, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.55 g (1.3 mmol) of 4-chloro-6-nitro-N-(3-phenylpropylthio)acetyl-anthranilic acid methyl ester are placed in 6 ml of tetrahydrofuran at 0° under nitrogen. 2.6 ml of a 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 1 hour at 0°. The reaction mixture is poured into 50 ml of 2N hydrochloric acid/ice and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated by evaporation. The residue is taken up in a small amount of ethyl acetate, and hexane is added until precipitation begins. The precipitate formed is filtered off with suction and dried. 374 mg (73% of theory) of 7-chloro-5-nitro-4-hydroxy-3-(3-phenylpropylthio)-2(1H)-quinolone are obtained in the form of red crystals having a melting point of 177°-184°.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. additionis added until precipitation
  6. customThe precipitate formed
  7. filtrationis filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-6937ac7543b0415098b30c4f53a96fa5
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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