Lithium Hexamethyldisilazide → HCID 15489350, compound

HRID 1954210Notes

Reaction equation

HRID 1954210 reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=2[F:24])(=[O:13])=[O:12])=[CH:6][CH:5]=1)[CH3:3].[CH3:25][Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH3:3][N:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:25])[S:11]([C:14]2[C:15]([F:24])=[C:16]([F:23])[C:17]([F:22])=[C:18]([F:21])[C:19]=2[F:20])(=[O:13])=[O:12])=[CH:6][CH:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 9842096HCID 9842096, compound

Product 1

HCID 15489350HCID 15489350, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(N,N-Dimethylamino)-1-(pentafluorophenylsulfonamido)benzene (100 mg, 0.273 mmol) was dissolved in dry THF (2.5 mL) and to the system was added under N2 at room temperature a 1M solution of lithium bis(trimethylsilyl)amide (0.274 mL). The reaction mixture was stirred for 10 min followed by addition of Mel (65 mg, 0.028 mL). The reaction mixture was stirred overnight, the solvent was evaporated under reduced pressure and the crude product purified by HPLC using silica as the stationary phase and eluting with 20% EtOAc/Hex (v/v) to afford the product as a white solid in 60% yield (62 mg). EI m/z: 380(35, M+), 149(100). 1H NMR (CD3OD) 7.05(d, J=8 Hz, 2H), 6.68(d, J=8 Hz, 2H), 3.33(s, 3H) 2.93(s, 6H). Anal. calcd. for C15H13F5SO2N2 : C, 47.37, H, 3.45, N 7.37. Found: C, 47.37, H, 3.49, N, 7.32.

Workup

  1. additionfollowed by addition of Mel (65 mg, 0.028 mL)
  2. stirringThe reaction mixture was stirred overnight
  3. customthe solvent was evaporated under reduced pressure
  4. customthe crude product purified by HPLC
  5. washeluting with 20% EtOAc/Hex (v/v)

Sources & evidence

ORD record
ord-6311f86b1f124212aa63b84aec2ba1d9
Source dataset
uspto-grants-2000_09
Patent number
US06121304

Reaction notes

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