Phosphorus oxychloride → HCID 14953117, compound

HRID 1493328Notes

Reaction equation

HRID 1493328 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16][C:17]([CH3:23])([CH3:22])[CH2:18][C:19]([NH2:21])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16][C:17]([CH3:22])([CH3:23])[CH2:18][C:19]#[N:21])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14953116HCID 14953116, compound

Product 1

HCID 14953117HCID 14953117, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.7 g of 4-[1-(4-chlorobenzyl)benzimidazol-2-yl]-3,3-dimethylbutanamide are dissolved in 50 ml of chloroform. 2.3 ml of phosphorus oxychloride are added and the mixture is refluxed for 5 hours. After cooling, the solvents are evaporated off under vacuum and the residue is taken up with water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness under vacuum to give an oil which crystallizes from ether. The crystals are filtered off, washed with ether and then dried to give 2.5 g of 4-[1-(4-chlorobenzyl)benzimidazol-2-yl]-3,3-dimethylbutyronitrile in the form of crystals melting at 110° C.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. customthe solvents are evaporated off under vacuum
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated to dryness under vacuum
  7. customto give an oil which
  8. customcrystallizes from ether
  9. filtrationThe crystals are filtered off
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-00f9e1b729534e9094d31d1534b9af23
Source dataset
uspto-grants-1991_06
Patent number
US05021443

Reaction notes

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