Sodium bis(trimethylsilyl)amide → HCID 54737669, compound

HRID 1781625Notes

Reaction equation

HRID 1781625 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[NH:6][C:7](=[O:17])[CH2:8][S:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:22][C:19]1[CH:18]=[C:5]2[C:4]([C:3]([OH:2])=[C:8]([S:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:7](=[O:17])[NH:6]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 22364779HCID 22364779, compound

Product 1

HCID 54737669HCID 54737669, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (5.6 mmol) of 4-chloro-N-(3-methoxycarbonylpropylthio)acetyl-anthranilic acid methyl ester are placed in 20 ml of tetrahydrofuran at 0° , and 16.8 ml of a 1M solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 30 minutes at 0° and the reaction mixture Is then poured into 2N hydrochloric acid/ice. The resulting white suspension is filtered with suction and the resulting colourless crystals are dried under a high vacuum at 60°. The dried product is made into a suspension in ethyl acetate and stirred for 30 minutes. The suspension is filtered, and the colourless crystals are dried under a high vacuum at 70°, yielding 7-chloro-4-hydroxy-3-(3-methoxycarbonyl-propylthio)-2(1H)-quinolone in the form of colourless crystals having a melting point of 183°-185° (decomp.).

Workup

  1. filtrationThe resulting white suspension is filtered with suction
  2. customthe resulting colourless crystals are dried under a high vacuum at 60°
  3. stirringstirred for 30 minutes
  4. filtrationThe suspension is filtered
  5. customthe colourless crystals are dried under a high vacuum at 70°

Sources & evidence

ORD record
ord-1d1ccd59bf5a48d8990196a9d96b64c4
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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