Sodium bis(trimethylsilyl)amide → HCID 18174672, compound

HRID 395385Notes

Reaction equation

HRID 395385 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[C:37][CH2:38][CH2:39][CH2:40]I)=[CH:32][CH:31]=1>CN(C=O)C>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH:37]([C:12]2([S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:10])=[O:11])[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])[CH2:38][CH2:39][CH3:40])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10613276HCID 10613276, compoundHCID 11771159HCID 11771159, compound

Product 1

HCID 18174672HCID 18174672, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-methoxyphenylsulfonyl)-thiazolidine-2,4-dione [U.S. Pat. No. 5,605,918; February 1997; Wrobel, et al.]((2.74 g, 9.5 mMol) in DMF (50 ml) was added sodium hexamethyldisilazide (1.0 M solution in THF—19.0 ml, 19.0 mmol) at room temperature, under nitrogen, and this was stirred for 15 minutes. To this was added 1-(4-chlorophenyl)-5-iodo-1-pentyne (2.70 g, 9.5 mmol) over 5 minutes, and this solution was stirred overnight at room temperature. The reaction mixture was quenched in water, and the solid that was obtained was recrystallized from methanol to give 1.59 g of the title compound as colorless crystals, m.p. 172-174°; NMR (CDCl3) δ 1.59 (m, 1H); 2.0 (m, 1H); 2.36 (dq (doublet of quartets?), 1H); 2.5 (t, 2H); 2.67 (dq, 1H); 3.88 (s, 3H); 7.0 (d, 2H); 7.26 (s, 4H) 7.86 (d, 2H).

Workup

  1. stirringthis solution was stirred overnight at room temperature
  2. customThe reaction mixture was quenched in water
  3. customthe solid that was obtained
  4. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-bb09030471f84f278238aaf32638a1b4
Source dataset
uspto-grants-2003_08
Patent number
US06605628B1

Reaction notes

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