Water → HCID 21546967, compound

HRID 1605492Notes

Reaction equation

HRID 1605492 reaction equation
[OH2:1].[OH:2][C:3]1([C:8]#[N:9])[CH2:7][CH:6]=[CH:5][CH2:4]1>C(O)(=O)C>[OH:2][C:3]1([C:8]([NH2:9])=[O:1])[CH2:7][CH:6]=[CH:5][CH2:4]1

Participants

4

Reactant 2

HCID 962WaterHCID 21546968HCID 21546968, compound

Product 1

HCID 21546967HCID 21546967, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5 ml. of a solution prepared by mixing one part of water and 9 parts of glacial acetic acid, and then cooling to 0°-10° C., is added 300 mg. of 1-hydroxy-3-cyclopentene-1-carbonitrile. To this is then added 5 ml. of a solution prepared by saturating glacial acetic acid with gaseous hydrogen bromide and cooling to 0°-10° C. The resulting mixture is allowed to stand at room temperature overnight. It is then evaporated to dryness in vacuo, and the residue is partitioned between ethyl acetate and 5% sodium bicarbonate solution. The ethyl acetate layer is separated, and then dried using anhydrous magnesium sulfate. Removal of the ethyl acetate by evaporation in vacuo affords 1-hydroxy-3-cyclopentene-1-carboxamide.

Workup

  1. customof a solution prepared
  2. temperaturecooling to 0°-10° C.
  3. additionis added 300 mg
  4. additionTo this is then added 5 ml
  5. customof a solution prepared
  6. concentrationby saturating glacial acetic acid with gaseous hydrogen bromide
  7. temperaturecooling to 0°-10° C
  8. customIt is then evaporated to dryness in vacuo
  9. customthe residue is partitioned between ethyl acetate and 5% sodium bicarbonate solution
  10. customThe ethyl acetate layer is separated
  11. customdried
  12. customRemoval of the ethyl acetate
  13. customby evaporation in vacuo

Sources & evidence

ORD record
ord-447c3f7bdc3e4f36b5affc3e5cb92540
Source dataset
uspto-grants-1976_04
Patent number
US03950390

Reaction notes

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