Sodium hydride → HCID 22339406, compound

HRID 1006207Notes

Reaction equation

HRID 1006207 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:21]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[CH:23]=[N:22]2)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=1.[H-].[Na+].[CH3:31][Si:32]([CH2:35][CH2:36][O:37][CH2:38]Cl)([CH3:34])[CH3:33]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:21]2[C:26](=[O:27])[N:25]([CH2:38][O:37][CH2:36][CH2:35][Si:32]([CH3:34])([CH3:33])[CH3:31])[C:24](=[O:28])[CH:23]=[N:22]2)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 22339380HCID 22339380, compound

Product 1

HCID 22339406HCID 22339406, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[3,5-dichloro-4-(4-methoxy-3-nitro-phenoxy)-phenyl]-2H-[1,2,4]-triazin-3,5-dione (1.32 g, 3.1 mmol) in 12 mL of DMF at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.15 g, 3.7 mmol). After stirring at 0° C. for 5 min, the mixture was stirred at room temperature for 30 min as a clear reddish brown solution. To the solution at room temperature was added SEMCl (0.63 g, 3.74 mmol). After stirring at room temperature for 20 h, the solution was diluted with H2O (30 mL) and extracted with EtOAc (2×50 mL). The combined EtOAc extracts were washed with 1N HCl (100 mL), H2O (3×50 mL), brine (100 mL), dried and concentrated. The residue was dissolved in CH2Cl2followed by addition of ether to give the title compound (0.83 g) of Step A as light brown crystals. NMR (400 Mhz, CD3OD) d 0.02 (m, 9H), 1.01 (m, 2H), 3.75 (m, 2H), 5.45 (s, 2H).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min as a clear reddish brown solution
  2. stirringAfter stirring at room temperature for 20 h
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined EtOAc extracts were washed with 1N HCl (100 mL), H2O (3×50 mL), brine (100 mL)
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in CH2Cl2followed by addition of ether

Sources & evidence

ORD record
ord-b17dc637bcc24c1da5a3f21a79489d0e
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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