Ammonium Chloride → HCID 69072763, compound

HRID 1454931Notes

Reaction equation

HRID 1454931 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Br:14])[C:12]=1[CH3:13].[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16].[NH4+].[Cl-]>CCCCCC>[Br:14][C:11]1[CH:10]=[N:9][CH:8]=[C:7]([C:12]=1[CH3:13])[C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 62412tert-Butyl isocyanateHCID 8193383,5-Dibromo-4-methylpyridine2×HCID 178418339Butyllithium

Product 1

HCID 69072763HCID 69072763, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-100 °C

Procedure

Under argon, an n-butyllithium solution in hexane (1.55N, 6.6 ml) is added dropwise to a solution of 3,5-dibromo-4-methylpyridine (intermediate 10.1, 2.51 g, 10 mmol) kept at −100° C. After stirring for 10 min, tert-butyl isocyanate (2.28 ml, 20 mmol) is added. The stirring is maintained for 20 min at −100° C. and then for 1 h at −78° C. and at room temperature overnight. An aqueous NH4Cl solution is added to the reaction mixture. Extraction with AcOEt/H2O gives a brown solid which is taken up in an AcOEt/petroleum ether mixture. The compound obtained is isolated by filtration.

Workup

  1. customkept at −100° C
  2. waitfor 1 h at −78° C.
  3. customat room temperature
  4. customovernight
  5. extractionExtraction with AcOEt/H2O
  6. customgives a brown solid which
  7. customThe compound obtained
  8. customis isolated by filtration

Sources & evidence

ORD record
ord-797dc3b8945d4f4ea7760241cb3fd620
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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