Phosphorus oxychloride → HCID 21251007, compound

HRID 1531836Notes

Reaction equation

HRID 1531836 reaction equation
[C:1]1([N:7]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[NH:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][CH:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=2[NH:9]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21251008HCID 21251008, compound

Product 1

HCID 21251007HCID 21251007, compoundYield 32.2%

Procedure

A mixture of 2.3 g (0.0107 mol) of 1-phenyl-4,5,6,7-tetrahydro-2H-benzimidazol-2-one and 30 ml of POCl3 is stirred under reflux for 6 hours. The excess POCl3 is evaporated under vacuum and the residue is hydrolyzed with water and concentrated ammonium hydroxide. The mixture is extracted twice with methylene chloride, evaporated and the residue is purified by flash chromatography on silica with an 80:20 heptane/ethyl acetate eluent. 0.8 g of product is recovered. Yield=32.2%.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe excess POCl3 is evaporated under vacuum
  3. extractionThe mixture is extracted twice with methylene chloride
  4. customevaporated
  5. customthe residue is purified by flash chromatography on silica with an 80:20 heptane/ethyl acetate eluent
  6. custom0.8 g of product is recovered

Sources & evidence

ORD record
ord-f83aa7d79d154b56894e3ddcb936b761
Source dataset
uspto-grants-2001_03
Patent number
US06200991B1

Reaction notes

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