Hydrogen Sulfide → HCID 21866459, compound

HRID 1582912Notes

Reaction equation

HRID 1582912 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:16]#[N:17])=[C:13]([CH3:15])[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[SH2:25]>N1C=CC=CC=1>[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:16](=[S:25])[NH2:17])=[C:13]([CH3:15])[N:14]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 21866517HCID 21866517, compound

Product 1

HCID 21866459HCID 21866459, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(N-BOC-Aminomethyl)-5-cyano-4-methylthiazole [sic] (7.5 g, 29.61 mmol) was dissolved in pyridine (30 ml), and triethylamine (27 ml) was added. The solution was saturated with hydrogen sulfide at 0° C. and then left to stand for 48 hours at room temperature. The solvent was subsequently removed on a rotary evaporator, and the residue was taken up in ethyl acetate, washed with 20% strength potassium hydrogen sulfate solution and dried over magnesium sulfate. The solvent was removed on a rotary evaporator, and the crude product was dissolved in dichloromethane and precipitated with petroleum ether. The product which had precipitated was filtered off with suction and dried in a vacuum drying oven [lacuna] 40° C. Yield: 7.1 g (24.7 mmol, 83%).

Workup

  1. waitleft
  2. customThe solvent was subsequently removed on a rotary evaporator
  3. washwashed with 20% strength potassium hydrogen sulfate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed on a rotary evaporator
  6. dissolutionthe crude product was dissolved in dichloromethane
  7. customprecipitated with petroleum ether
  8. customThe product which had precipitated
  9. filtrationwas filtered off with suction
  10. customdried in a vacuum
  11. customdrying oven [lacuna] 40° C

Sources & evidence

ORD record
ord-c18d6dad05ca4a40bbf7b0af8544c62c
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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