Hydrogen Sulfide → HCID 21866462, compound

HRID 1582915Notes

Reaction equation

HRID 1582915 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:19]#[N:20])=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[SH2:28]>N1C=CC=CC=1>[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:19](=[S:28])[NH2:20])=[C:13]([C:15]([F:17])([F:18])[F:16])[N:14]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 21866452HCID 21866452, compound

Product 1

HCID 21866462HCID 21866462, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(N-BOC-Aminomethyl)-5-cyano-4-trifluoromethylthiazole [sic] (4.6 g, 14.97 mmol) was dissolved in pyridine (20 ml), triethylamine (24 ml) was added, and the solution was saturated with hydrogen sulfide. After two days at room temperature, the solvent was removed on a rotary evaporator. The crude product was taken up in ethyl acetate and washed in succession with 20% strength sodium hydrogen sulfate solution and water. After drying (MgSO4), the solvent was removed on a rotary evaporator. The crude product was purified by flash chromatography. Yield: 2.5 g (7.32 mmol, 49%).

Workup

  1. customthe solvent was removed on a rotary evaporator
  2. washwashed in succession with 20% strength sodium hydrogen sulfate solution and water
  3. dry with materialAfter drying (MgSO4)
  4. customthe solvent was removed on a rotary evaporator
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-0772b6b0138446a5b3d5f3b4e78a9fc6
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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