Phosphorus oxychloride → HCID 19819790, compound

HRID 1031174Notes

Reaction equation

HRID 1031174 reaction equation
O[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.P(Cl)(Cl)([Cl:13])=O>>[ClH:13].[Cl:13][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517141HCID 178517141, compound

Product 1

HCID 19819790HCID 19819790, compound

Procedure

A mixture of 2-hydroxybenzimidazole (200 g) and phosphorus oxychloride (1100 ml) was heated at reflux temperature for 1 hr and HCl gas was bubbled into the mixture for 3.5 hr. The excess phosphorus oxychloride was removed on a rotary evaporator. The residual oil was poured into ice water (2 L) and a solid impurity was removed by filtration. The filtrate was basified to pH 8 with concentrated ammonium hydroxide. The solid product was collected and dried at 60° C. in vacuo for 18 hrs. The product was recrystallized from acetone to obtain 70 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hr
  3. customHCl gas was bubbled into the mixture for 3.5 hr
  4. customThe excess phosphorus oxychloride was removed on a rotary evaporator
  5. additionThe residual oil was poured into ice water (2 L)
  6. customa solid impurity was removed by filtration
  7. customThe solid product was collected
  8. customdried at 60° C. in vacuo for 18 hrs
  9. customThe product was recrystallized from acetone

Sources & evidence

ORD record
ord-074a95078b424aa6b40f73d3ac8a9e08
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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