Sodium bis(trimethylsilyl)amide → HCID 67726448, compound

HRID 1781637Notes

Reaction equation

HRID 1781637 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:20][C:21]([Cl:25])=[CH:22][C:23]=1[Cl:24])[NH:6][C:7](=[O:19])[CH2:8][S:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:24][C:23]1[CH:22]=[C:21]([Cl:25])[CH:20]=[C:5]2[C:4]=1[C:3]([OH:2])=[C:8]([S:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1)[C:7](=[O:19])[NH:6]2

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 53939424HCID 53939424, compound

Product 1

HCID 67726448HCID 67726448, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.2 g (5.31 mmol) of 4,6-dichloro-N-[3-(pyrimidin-5-yl)-propylthio]acetyl-anthranilic acid methyl ester are placed in 25 ml of tetrahydrofuran at 0° under nitrogen. 10.62 ml of a 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 2 hours at 0°. The reaction mixture is poured into 50 ml of 2N hydrochloric acid/ice and filtered. 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, washed with hexane and dried. 1.75 g (86.2% of theory) of 5,7-dichloro-4-hydroxy-3-[3-(pyrimidin-5-yl)propylthio)-2-(1H)-quinolone are obtained in the form of red crystals having a melting point of 252°-254°.

Workup

  1. filtrationfiltered
  2. additionis added until precipitation
  3. customThe precipitate formed
  4. filtrationis filtered off with suction
  5. washwashed with hexane
  6. customdried

Sources & evidence

ORD record
ord-9c4f46622cfe4c929ea83878701e7abd
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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