Tetrahydrofuran → HCID 15839665, compound

HRID 363526Notes

Reaction equation

HRID 363526 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([NH2:16])=[S:15])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C1COCC1.[CH3:24][N:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](=O)[CH2:31]Br>CCOC(C)=O>[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]3[S:15][C:30]([C:26]4[N:25]([CH3:24])[CH:29]=[CH:28][CH:27]=4)=[CH:31][N:16]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 124077412-Bromo-1-(1-methyl-1H-pyrrol-2-yl)ethan-1-oneHCID 53772023HCID 53772023, compound

Product 1

HCID 15839665HCID 15839665, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a 25 mL round bottomed flask with a stirring bar reflux condenser and an argon inlet is added 1-(4-cyanobenzyl)-5-(aminothiocarbonyl)methyl-1H-imidazole (0.12 g, 0.468 mmol), dry THF (10 mL), and N-methyl-a-bromoacetylpyrrole (0.098 g, 0.491 mmol). This mixture is heated at 50° C. for 7 hours. The cooled reaction mixture is diluted with EtOAc and washed sucessively with aq. NaHCO3, water, and brine. The organic extract is dried, (MgSO4) and the solvent is evaporated in vacuo. The residue is purified by chromatography to afford the title compound.

Workup

  1. temperatureTo a 25 mL round bottomed flask with a stirring bar reflux condenser and an argon inlet
  2. customThe cooled reaction mixture
  3. washwashed sucessively with aq. NaHCO3, water, and brine
  4. extractionThe organic extract
  5. customis dried
  6. custom(MgSO4) and the solvent is evaporated in vacuo
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-ec83389ff2e9450381e7f7d96dca43f4
Source dataset
uspto-grants-1999_02
Patent number
US05874452

Reaction notes

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