Water → HCID 66978037, compound

HRID 1846437Notes

Reaction equation

HRID 1846437 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:7]([NH2:8])=[C:6]([CH3:14])[CH:5]=1.[CH3:15]I.O>CN(C=O)C>[Br:3][C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:7]([NH:8][CH3:15])=[C:6]([CH3:14])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5226794-Bromo-2-methyl-6-nitroaniline

Product 1

HCID 66978037HCID 66978037, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.80 g (86.6 mmol) sodium hydride (55%, suspension in mineral oil) were added batchwise to 20.0 g (86.6 mmol) 4-bromo-2-methyl-6-nitroaniline in 250 mL DMF with slight cooling and the mixture was stirred for 30 min. Then 5.40 mL (86.6 mmol) methyl iodide were slowly added dropwise, the cooling was stopped and the mixture was stirred overnight at RT. Then water was slowly added while the mixture was cooled and it was extracted several times with EtOAc. The organic phases were combined, dried on sodium sulphate, filtered and evaporated down i.vac. The residue was recrystallised from DIPE, cooled and the precipitate was suction filtered and dried.

Workup

  1. temperaturewith slight cooling
  2. stirringthe mixture was stirred overnight at RT
  3. temperaturewas cooled
  4. extractionit was extracted several times with EtOAc
  5. customdried on sodium sulphate
  6. filtrationfiltered
  7. customevaporated down i.vac
  8. customThe residue was recrystallised from DIPE
  9. temperaturecooled
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-b153b4eaa70f4d99b56c7361c6913aa0
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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