Iodoethane → HCID 69356918, compound

HRID 852601Notes

Reaction equation

HRID 852601 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].[CH2:22](I)[CH3:23]>CN(C=O)C>[NH2:12][C:11]1[C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[NH:1][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 69356421HCID 69356421, compound

Product 1

HCID 69356918HCID 69356918, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3,4-diamino-5-nitrobenzoate (D204) (1.5 g, 7.1 mmol, 1 equiv) in DMF (30 ml) at room temperature was added K2CO3 (2.2 g, 16.0 mmol, 2.25 equiv) then ethyl iodide (1.28 ml, 16.0 mmol, 2.25 equiv). The resulting suspension was stirred at 60° C. for 2 h then ethyl iodide (1 ml, 12.5 mmol, 1.8 equiv) was added and the resulting mixture stirred for another 6 h then cooled to room temperature and partitioned between AcOEt and a saturated aqueous NaHCO3 solution. The two layers were separated and the organic phase washed with H2O, dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O to give methyl 4-amino-3-(ethylamino)-5-nitrobenzoate (D205) (0.85 g, 50%) as a red solid which was used in the next step without further purification. [M+H]+=240.2, RT=2.95 min.

Workup

  1. stirringthe resulting mixture stirred for another 6 h
  2. temperaturethen cooled to room temperature
  3. custompartitioned between AcOEt
  4. customThe two layers were separated
  5. washthe organic phase washed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-f3924eb7413b48dc86ddbd3e0f110a8b
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…