Propionyl chloride → HCID 136110714, compound

HRID 1614325Notes

Reaction equation

HRID 1614325 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[NH:13])[NH:11][OH:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].[C:14](Cl)(=O)[CH2:15][CH3:16]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:13]=[C:14]([CH2:15][CH3:16])[O:12][N:11]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 178513332HCID 178513332, compound

Product 1

HCID 136110714HCID 136110714, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 14.1 parts of 3,5-dichloro-N,4-dihydroxybenzenecarboximidamide, 6.5 parts of propanoylchloride and 98 parts of pyridine was stirred for 4 hours at reflux temperature. The reaction mixture was concentrated and the residue was partitioned between water and dichloromethane. The organic layer was separated and washed successively with water (2×) and NaCl (dil.). The combined aqueous layers were washed with dichloromethane and then filtered over diatomaceous earth. After acidifying with acetic acid, the precipitate was filtered off and taken up in dichloromethane. This solution was dried, filtered and evaporated. The residue was crystallized from a mixture of ethanol and water. The product was filtered off and dried in vacuo at 50° C., yielding 4.25 parts (25.6%) of 2,6-dichloro-4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenol; mp. 125.7° C. (interm. 11).

Workup

  1. temperatureat reflux temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between water and dichloromethane
  4. customThe organic layer was separated
  5. washwashed successively with water (2×) and NaCl (dil.)
  6. washThe combined aqueous layers were washed with dichloromethane
  7. filtrationfiltered over diatomaceous earth
  8. filtrationthe precipitate was filtered off
  9. customThis solution was dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was crystallized from a mixture of ethanol and water
  13. filtrationThe product was filtered off
  14. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-91baad77b30d48799129d47bc6a44ffe
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

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