Ethyl Acetate → HCID 57855960, compound

HRID 2039617Notes

Reaction equation

HRID 2039617 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH:11][CH3:12])=[C:6]([Cl:13])[C:5]=1[NH2:14].[C:16](O)(=O)C.C(N)=N.CCOC(C)=O>CCO>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH2:14])=[C:6]([Cl:13])[C:7]2[N:11]([CH3:16])[CH:12]=[N:10][C:8]=2[CH:9]=1)=[O:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 57855886HCID 57855886, compound

Product 1

HCID 57855960HCID 57855960, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1 g (4.35 mmol) of 2,5-diamino-3-chloro-4-methylamino-benzoic acid methyl ester in 153 ml of EtOH, is added 700 mg (6.53 mmol) of formamidine acetate. The mixture is stirred at a temperature of 80° C. for 24 hours. EtOAc is added and the organic phase is washed once with H2O and once with brine. Then the organic layer is dried on Na2SO4, filtrated and concentrated. After purification by flash chromatography on silica gel 0.68 g (2.84 mmol, 65%) of a dark violet solid were obtained. LC/MS: 240/242 (M+1)+.

Workup

  1. washthe organic phase is washed once with H2O and once with brine
  2. customThen the organic layer is dried on Na2SO4
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customAfter purification by flash chromatography on silica gel 0.68 g (2.84 mmol, 65%) of a dark violet solid
  6. customwere obtained

Sources & evidence

ORD record
ord-d7e60d9e0a9c4515bff0b9f90ab720e9
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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