Hydrogen Sulfide → HCID 178446445, compound

HRID 980135Notes

Reaction equation

HRID 980135 reaction equation
[CH2:1]([NH:6][C:7]([NH:9][C:10]#[N:11])=[NH:8])[CH2:2][CH2:3][CH2:4][CH3:5].C(NCC)C.[SH2:17]>CO>[CH2:1]([NH:6][C:7]([NH:9][C:10]([NH2:11])=[S:17])=[NH:8])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8021DiethylamineHCID 178446444N-Pentyl-N'-cyanoguanidine

Product 1

HCID 178446445HCID 178446445, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Pentyl-N'-cyanoguanidine (30.0 g, 0.195 mol) and diethylamine (3 ml) were combined in methanol (550 ml). This solution was cooled to -40°, saturated with hydrogen sulfide gas, transferred to a stainless steel bomb and heated at 85° for 40 hours. The excess hydrogen sulfide was purged from the reaction mixture with nitrogen and the solution was then concentrated in vacuo. The residue was flash chromatographed (140 mm column, 5% methanol in chloroform). The fractions containing pure product were combined and evaporated yielding 22.01 g (59.9%) of white solid. A portion was recrystallized from chloroform to furnish material with mp 98°-100°, mass spec.: M+ 188.

Workup

  1. temperatureheated at 85° for 40 hours
  2. customThe excess hydrogen sulfide was purged from the reaction mixture with nitrogen
  3. concentrationthe solution was then concentrated in vacuo
  4. customchromatographed (140 mm column, 5% methanol in chloroform)
  5. additionThe fractions containing pure product
  6. customevaporated

Sources & evidence

ORD record
ord-2861fade1aee4d5498002a84f478adeb
Source dataset
uspto-grants-1987_01
Patent number
US04636498

Reaction notes

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