Butyl isocyanate → HCID 22632873, compound

HRID 2270220Notes

Reaction equation

HRID 2270220 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+].[CH2:23]([N:27]=[C:28]=[O:29])[CH2:24][CH2:25][CH3:26]>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:27]([CH2:23][CH2:24][CH2:25][CH3:26])[C:28]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 24758Sodium hydrideHCID 22632919HCID 22632919, compound

Product 1

HCID 22632873HCID 22632873, compoundYield 58.4%

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 n-butyl isocyanate (2.14 mL, 19.02 mmol) in DMA afforded crude product. Recrystallization from chloroform provided 1.40 g of the title compound as a solid, mp 147-148° C.

Workup

  1. customafforded crude product
  2. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-e36b9f9b64854c98a31337cc3d36c58a
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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