Ethyl chloroformate → HCID 86635792, compound

HRID 2202838Notes

Reaction equation

HRID 2202838 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[H-].[Na+].Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15].[NH4+].[Cl-]>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[NH:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([CH3:10])[C:5]=1[NH2:9])[CH3:18]

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 15163975-Bromo-3-methylbenzene-1,2-diamine

Product 1

HCID 86635792HCID 86635792, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 5-bromo-3-methylbenzene-1,2-diamine (4 g) in DMF (80 ml) was added NaH (40% oil dispersion, 800 mg) at 0° C., and the reaction mixture was stirred for another 30 min at the same temperature. A solution of ethyl chloroformate (1.9 g) in DMF (10 ml) was added dropwise thereto at 0° C. and then the resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was poured into saturated NH4Cl solution, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (2.5 g) as a yellow solid.

Workup

  1. customat 0° C. and then the resulting reaction mixture
  2. stirringwas stirred at room temperature for 1 h
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-6922ce521faf4ae4a99274a4e5d79f35
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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