Isoamyl Nitrite → HCID 12832301, compound

HRID 370763Notes

Reaction equation

HRID 370763 reaction equation
Cl.[C:2]1([C:8]2[N:9]=[C:10]([S:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=3N)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OCCC(C)C)=O>Cl>[C:13]1([C:12]2[N:11]=[C:10]([S:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=3)[NH:9][C:8]=2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 20275410HCID 20275410, compound

Product 1

HCID 12832301HCID 12832301, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2.24 g of 4,5-diphenyl-2-(2-amino-4-trifluoromethylphenylthio)imidazole hydrochloride is dissolved in 100 ml of methanolic hydrochloric acid and combined at 0° with 0.586 g of isoamyl nitrite. The mixture is agitated for 30 minutes, then heated to boiling for 2 hours and the solution evaporated under vacuum to dryness. The residue is distributed between ethyl acetate and sodium bicarbonate solution. The organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized from ether/chloroform, thus obtaining 1.61 g of 4,5-diphenyl-2-(4-trifluoromethylphenylthio)imidazole, mp 227°-229°.

Workup

  1. temperatureheated
  2. waitto boiling for 2 hours
  3. customthe solution evaporated under vacuum to dryness
  4. dry with materialThe organic solution is dried over sodium sulfate
  5. concentrationconcentrated to dryness under vacuum
  6. customThe residue is crystallized from ether/chloroform

Sources & evidence

ORD record
ord-e47298062d5947c9be5805047d3c97ff
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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