Phosphorus oxychloride → HCID 67271832, compound

HRID 1698530Notes

Reaction equation

HRID 1698530 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:21])=O>C(OCC)(=O)C>[Cl:21][C:3]1[N:2]([CH3:1])[C:6]2[C:7]([CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 672728231,3-Dihydro-1-methyl-7-(1-propylbutyl)-2H-benzimidazol-2-one

Product 1

HCID 67271832HCID 67271832, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

The crude 1-methyl-7-(1-propylbutyl)-1,3-dihydrobenzimidazol-2-one (710 mg, 2.88 mmol) was dissolved in 10 mL of phosphorous oxychloride and heated at 100° C. overnight. The reaction was allowed to cool to room temperature and concentrated in vacuo. The residue thus obtained was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to give 655 mg (86%) of the title compound, which was used in the next step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue thus obtained
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a646376413f14ef4af0f3322d998eac5
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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