Cyclopropanecarboxylic acid → HCID 89691201, compound

HRID 2202840Notes

Reaction equation

HRID 2202840 reaction equation
[CH:1]1([C:4](O)=O)C[CH2:2]1.[Br:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([NH:15][CH3:16])=[C:10]([CH3:17])[CH:9]=1.[C:18]([O-])(O)=O.[Na+]>O=P(Cl)(Cl)Cl>[Br:7][C:8]1[CH:9]=[C:10]([CH3:17])[C:11]2[N:15]=[C:16]([CH:4]3[CH2:1][CH2:2]3)[N:14]([CH3:18])[C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 15655Cyclopropanecarboxylic acidHCID 516892Sodium BicarbonateHCID 53408110HCID 53408110, compound

Product 1

HCID 89691201HCID 89691201, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of cyclopropanecarboxylic acid (356 μl) and 5-bromo-N′,3-dimethylbenzene-1,2-diamine (600 mg) was added POCl3 (10 ml), and the mixture was heated at 120° C. After 3 h, the mixture was poured into saturated aqueous NaHCO3 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 (450 mg) as brown solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-bacaa5e545244354a47be1f14f32e8f4
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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