Sodium hydride → HCID 23047247, compound

HRID 2107046Notes

Reaction equation

HRID 2107046 reaction equation
[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2([CH3:20])[CH3:19].[H-].[Na+].ClC(Cl)(Cl)[C:25]([N:27]=C=O)=[O:26]>CN(C=O)C.C(Cl)Cl>[CH3:1][CH:2]1[S:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:25]([NH2:27])=[O:26])[C:13](=[O:18])[C:12]2([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76400Trichloroacetyl isocyanateHCID 15111517HCID 15111517, compound

Product 1

HCID 23047247HCID 23047247, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.45 g (5 mmol) 5-(3,6-dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (Example 3) in 30 ml DMF were cooled to 0° C. 0.12 g (5 mmol) sodium hydride from a 55% dispension in mineral oil was added and the mixture was stirred for 0.5 hr at 0° C. then 0.5 hr at 20° C. After cooling to 0° C. a solution of 1 g trichloroacetyl isocyanate in 5 ml dry methylene chloride was added dropwise. The reactional mixture was stirred at room temperature overnight. The solvent was evaporated under vacuum, the residue taken up in 50 ml ethyl acetate and 40 g neutral aluminum oxide was added. The compound was then extracted from the aluminum oxide on a column with ethyl acetate. The solvent was evaporated and the residue was purified by chromatography on silica (eluent:methylene chloride/ethyl acetate: 2/1) to yield 0.37 g (22%) of the desired compound.

Workup

  1. custom0.5 hr
  2. customat 20° C
  3. additionwas added dropwise
  4. stirringThe reactional mixture was stirred at room temperature overnight
  5. customThe solvent was evaporated under vacuum
  6. addition40 g neutral aluminum oxide was added
  7. extractionThe compound was then extracted from the aluminum oxide on a column with ethyl acetate
  8. customThe solvent was evaporated
  9. customthe residue was purified by chromatography on silica (eluent:methylene chloride/ethyl acetate: 2/1)

Sources & evidence

ORD record
ord-1b835a8dd59e4dcfbb7f229518bb30ae
Source dataset
uspto-grants-1990_06
Patent number
US04933336

Reaction notes

Loading…