Thioacetamide → HCID 86643647, compound

HRID 2240648Notes

Reaction equation

HRID 2240648 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:28])[NH:17][CH:18]3[CH2:23][CH2:22][CH:21]([C:24](=O)[CH2:25]Br)[CH2:20][CH2:19]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:29]([NH2:32])(=[S:31])[CH3:30]>C(#N)C>[CH:3]1[C:4]2[CH:12]([CH2:14][O:15][C:16](=[O:28])[NH:17][CH:18]3[CH2:19][CH2:20][CH:21]([C:24]4[N:32]=[C:29]([CH3:30])[S:31][CH:25]=4)[CH2:22][CH2:23]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:13]=[CH:1][CH:2]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 86643648HCID 86643648, compound

Product 1

HCID 86643647HCID 86643647, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.00 g (7 mmol) of 9H-fluoren-9-ylmethyl[4-(2-bromoacetyl)cyclohexyl]carbamate (cis compound) and 0.700 g (9 mmol) of thioacetamide are refluxed in 50 mL of acetonitrile for 72 hours with stirring. Then the reaction mixture is concentrated by evaporation, the residue is purified by chromatography. Corresponding fractions are combined and evaporated to dryness. The crystalline residue is extracted with diisopropyl ether and suction filtered. Yield: 1.10 g (39%) of cis compound; NMR: LH201648; m.p.: 140° C.-141° C.

Workup

  1. concentrationThen the reaction mixture is concentrated by evaporation
  2. customthe residue is purified by chromatography
  3. customevaporated to dryness
  4. extractionThe crystalline residue is extracted with diisopropyl ether and suction
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2de6c9dd9ce04c528c0f23f61137f316
Source dataset
uspto-grants-2010_05
Patent number
US07723381B2

Reaction notes

Loading…