Isoamyl Nitrite → HCID 12832301, compound

HRID 1995193Notes

Reaction equation

HRID 1995193 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-a5fbcd2c4def4eee96e3ebeb6b4bfddf
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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