Sodium hydride → HCID 22632933, compound

HRID 2270228Notes

Reaction equation

HRID 2270228 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][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=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:31]([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=2)[C:32]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 794431-Isocyanato-4-methoxybenzeneHCID 22632919HCID 22632919, compound

Product 1

HCID 22632933HCID 22632933, compoundYield 68.2%

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-methoxyphenyl isocyanate (1.31 mL, 9.51 mmol) in DMA afforded crude product. Recrystallization from chloroform provided 1.85 g of the title compound as a solid. mp 238-240° C.

Workup

  1. customafforded crude product
  2. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-67e2ffa647ff4fa89ce8312592bb53c4
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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