Isoamyl Nitrite → HCID 13315128, compound

HRID 569035Notes

Reaction equation

HRID 569035 reaction equation
N[C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(ON=O)CC(C)C.[CH2:23]([S:25]SCC)[CH3:24]>>[CH2:23]([S:25][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH3:24]

Participants

4

Reactant 3

HCID 8053Isoamyl Nitrite2×HCID 8077Diethyl disulfideHCID 1195373-Aminonorharman

Product 1

HCID 13315128HCID 13315128, compound

Conditions

Temperature
80 °C

Procedure

732 mg of 3-amino-β-carboline in 7 ml of diethyldisulfide are heated to 80° C. and mixed with 1 ml of isoamylnitrite. After 0.5 hours of heating to 80° C., it is again mixed with 1 ml of isoamylnitrite and heated to 80° C. for 1.5 hours. After distilling off, the residue is chromatographed twice on silica gel with ethyl acetate/cyclohexane as eluant. After absorptive precipitation of the corresponding evaporated fraction with cyclohexane/diisopropyl ether, 206 mg of 3-ethylthio-β-carboline with a 132°-133° C. melting point are obtained.

Workup

  1. temperatureheated to 80° C. for 1.5 hours
  2. distillationAfter distilling off
  3. customthe residue is chromatographed twice on silica gel with ethyl acetate/cyclohexane as eluant
  4. customAfter absorptive precipitation of the corresponding evaporated fraction with cyclohexane/diisopropyl ether, 206 mg of 3-ethylthio-β-carboline with a 132°-133° C.
  5. customare obtained

Sources & evidence

ORD record
ord-dc7e694bfb1946e5ab73d7098c2a6bc6
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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