Sodium hydride → HCID 15391306, compound

HRID 1451821Notes

Reaction equation

HRID 1451821 reaction equation
[H-].[Na+].[C:3]1([C:9]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:10]2[C:14](=[O:15])[CH:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[S:12][C:11]2=[O:26])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:40]1[CH:41]=[C:42]([C:47]#[C:48][CH2:49]Br)[CH:43]=[C:44](F)[CH:45]=1.[NH4+].[Cl-:52]>CN(C=O)C.O>[C:33]1([C:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:10]2[C:14](=[O:15])[C:13]([CH2:49][C:48]#[C:47][C:42]3[CH:43]=[CH:44][C:45]([Cl:52])=[CH:40][CH:41]=3)([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[S:12][C:11]2=[O:26])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10577722HCID 10577722, compound2×HCID 19973049HCID 19973049, compound

Product 1

HCID 15391306HCID 15391306, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (80% dispersion in mineral oil, 93 mg, 3.10 mmol) was added to a solution of N-(triphenylmethyl)-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione [(VI), from Example 34, 1.06 g, 2.07 mmol) in dry DMF (9 mL) at 0° C. under a dry N2 atmosphere. After 20 min, [3-(4-chlorophenyl)-prop-2-ynyl]-bromide [(IX), from Example 21, 0.52 g, 2.27 mmol] was added and the reaction mixture was stirred an additional 20 min at 0° C. Saturated aqueous NH4Cl (60 mL) was added, followed by water (60 mL). After stirring for 10 min, the solid was filtered, washed with water and triturated with petroleum ether to provide the title compound as a grey solid (1.16 g, 90%): mp 221°-223° C.; NMR (CDCl3): δ7.80 (d, J=8.2 Hz, 2H, ArH), 7.45 (d, J=7.5 Hz, 6H, CPh3H), 7.35 (d, J=8.2 Hz, 2H, ArH), 7.14 (m, 11H, Ar'H, CPh3H), 6.98 (d, J=8.5 Hz, 2H, Ar'H), 3.29 (d, J=16.7 Hz, 1H, CH2), 3.12 (d, J=16.7 Hz, 1H, CH2), 2.46 (s, 3H, CH3).

Workup

  1. customat 0° C.
  2. stirringAfter stirring for 10 min
  3. filtrationthe solid was filtered
  4. washwashed with water
  5. customtriturated with petroleum ether

Sources & evidence

ORD record
ord-a2a23b4fc5fe4ce0b738fbcf1f22df3e
Source dataset
uspto-grants-1997_02
Patent number
US05605918

Reaction notes

Loading…