Propionic Acid → HCID 136093171, compound

HRID 2049902Notes

Reaction equation

HRID 2049902 reaction equation
[F:1][S:2]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([S:12]([F:15])(=[O:14])=[O:13])[CH:11]=1)[NH2:8])(=[O:4])=[O:3].[N:16](OCCC(C)C)=O.[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32])#[N:25].C(O)(=O)CC>N1C=CC=CC=1.C(O)(=O)C.C1COCC1.C(O)C>[C:24]([C:26]1[CH:31]=[C:30]([N:16]=[N:8][C:7]2[CH:6]=[C:5]([S:2]([F:1])(=[O:4])=[O:3])[CH:11]=[C:10]([S:12]([F:15])(=[O:13])=[O:14])[CH:9]=2)[CH:29]=[CH:28][C:27]=1[OH:32])#[N:25]

Participants

9

Reactant 4

HCID 1032Propionic AcidHCID 8053Isoamyl NitriteHCID 119072-HydroxybenzonitrileHCID 19369074HCID 19369074, compound

Product 1

HCID 136093171HCID 136093171, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 25.7 g. (0.1 mol) 3,5-difluorosulfonylaniline in 100 ml. ethanol and 50 ml. THF is cooled below 10° C. and diazotized by adding 12 g. (0.1+mol) isoamyl nitrite slowly. After the addition, the run is stirred in an ice bath for about 15 min. The solution of diazonium salt is added in portions to a mixture of 11.9 g. (0.1 mol) of o-cyanophenol in 120 ml. mixed acid (1 volume propionic acid and 5 volumes acetic acid) that have been converted to a solution with 25 ml. pyridine and cooled below 10° C. in an ice bath. The coupled mixture is stirred until all of the ice in the bath has melted. Stirring is continued for about 50 hr. at room temperature. Then the run is poured into 1.5 l. water and the insoluble oil is extracted with several portions of ethyl acetate. The combined extracts are washed with three portions of dilute HCl, dried and concentrated. The residue is treated with toluene and concentrated several times to remove acetic and/or propionic acid. The dark oil that remains is dissolved in dichloromethane, applied to a column of Florisil, and eluted with ethyl acetate. The yield of product is 2.8 g.

Workup

  1. additionA mixture of 25.7 g
  2. additionby adding 12 g
  3. additionAfter the addition
  4. stirringStirring
  5. waitis continued for about 50 hr
  6. customat room temperature
  7. additionThen the run is poured into 1.5 l
  8. extractionwater and the insoluble oil is extracted with several portions of ethyl acetate
  9. washThe combined extracts are washed with three portions of dilute HCl
  10. customdried
  11. concentrationconcentrated
  12. additionThe residue is treated with toluene
  13. concentrationconcentrated several times
  14. customto remove acetic and/or propionic acid
  15. dissolutionThe dark oil that remains is dissolved in dichloromethane
  16. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-811133856028467d8aa1cd2a663c4cb1
Source dataset
uspto-grants-1980_04
Patent number
US04199355

Reaction notes

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