Diethyl Ether → HCID 19739880, compound

HRID 2255169Notes

Reaction equation

HRID 2255169 reaction equation
N[C:2]1[N+:7]([O-:8])=[C:6]([CH2:9][C:10](CC(C)C)([CH3:12])[CH3:11])[C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:4][C:3]=1[CH2:25][OH:26].[CH3:27][S:28]SC.N(OCCC(C)C)=O.C(OCC)C>CC#N>[CH2:18]([O:17][C:5]1[C:6]([CH2:9][CH:10]([CH3:12])[CH3:11])=[N+:7]([O-:8])[C:2]([S:28][CH3:27])=[C:3]([CH2:25][OH:26])[N:4]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8053Isoamyl NitriteHCID 12232Dimethyl DisulfideHCID 178442690HCID 178442690, compound

Product 1

HCID 19739880HCID 19739880, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.55 Grams of 6-amino-5-hydroxymethyl-3-benzyloxy-2-isobutyl isobutylpyrazine 1-oxide and 6.75 ml of dimethyl disulfide were dissolved in 50 ml of CH3CN, and thereto was added 3.02 ml of isoamyl nitrite. The mixture was subjected to a reaction for 20 minutes at 70°-80° C., and the reaction mixture was cooled to room temperature, and mixed with 150 ml of diethyl ether. The resulting mixture was washed with water (100 ml×3), and the ether layer was dried over MgSO4. The solvent was removed by evaporation. The residue was purified by a silica gel chromatography (30% EtOAc-hexane), followed by recrystallization from isopropyl ether-n-hexane to obtain 2.17 g of colorless needle-like crystals (Compound E-52c) having a melting point of 88.5°-86.5° C.

Workup

  1. customThe mixture was subjected to a reaction for 20 minutes at 70°-80° C.
  2. washThe resulting mixture was washed with water (100 ml×3)
  3. dry with materialthe ether layer was dried over MgSO4
  4. customThe solvent was removed by evaporation
  5. customThe residue was purified by a silica gel chromatography (30% EtOAc-hexane)
  6. customfollowed by recrystallization from isopropyl ether-n-hexane

Sources & evidence

ORD record
ord-8affef0ac147429ea5879f9facf1e417
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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