Sodium hydride → HCID 22632973, compound

HRID 2270225Notes

Reaction equation

HRID 2270225 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C:12]1[C:13](Cl)=[N:14][C:15]([Cl:19])=[C:16]([F:18])[CH:17]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>CC(N(C)C)=O>[CH2:1]([O:8][N:9]1[C:10](=[O:11])[C:12]2[CH:17]=[C:16]([F:18])[C:15]([Cl:19])=[N:14][C:13]=2[N:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:23])=[CH:25][CH:26]=2)[C:31]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 693254-Methylphenyl isocyanateHCID 22632919HCID 22632919, compound

Product 1

HCID 22632973HCID 22632973, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using the General Method 5, the reaction of N-benzyloxy-2,6-dichloro-5-fluoro-3-pyridinecarboxamide (Example M-2, 2.00 g, 6.34 mmol) and 60% NaH in oil (300 mg, 7.52 mmol) with 4-methylphenyl isocyanate (1.20 mL, 9.51 mmol) in DMA afforded crude product. Recrystallization from chloroform provided 1.91 g of the title compound as a solid, mp 218-219° C.

Workup

  1. customafforded crude product
  2. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-f15e2bb85ca54fd399edabe596caf151
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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