Water → HCID 54028471, compound

HRID 1957681Notes

Reaction equation

HRID 1957681 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([OH:21])[CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:22][N:23]([CH3:27])[C:24](Cl)=[S:25].O>CN(C=O)C>[CH3:22][N:23]([CH3:27])[C:24](=[S:25])[O:21][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([C:3]23[CH2:4][CH:5]4[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]4)[CH2:12]2)[CH2:10]3)[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 19068273HCID 19068273, compound

Product 1

HCID 54028471HCID 54028471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

600 mg (20 mmol) of sodium hydride (80% in oil) and 50 ml of DMF were introduced into a round-bottomed flask under a stream of nitrogen. The mixture was cooled to 0° C. and a solution of 5.5 g (20 mmol) of 3-(1-adamantyl)-4-methoxyphenol in 100 ml of DMF was added dropwise, tand he mixture was stirred until the evolution of gas had ceased. A solution of 3.3 g (26 mmol) of dimethylthiocarbamoyl chloride in 50 ml of DMF was then added thereto and the mixture was stirred for eight hours at room temperature. The reaction medium was poured into water and extracted with ethyl acetate. The organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and hexane (70/30). After evaporation of the solvents, 3.1 g (46%) of the expected compound having a melting point of 162°-4° C., were recovered.

Workup

  1. stirringthe mixture was stirred for eight hours at room temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated out
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by chromatography on a column of silica
  9. washeluted with a mixture of dichloromethane and hexane (70/30)
  10. customAfter evaporation of the solvents, 3.1 g (46%) of the expected compound
  11. customwere recovered

Sources & evidence

ORD record
ord-888a4d2b87394b6ca0878abdbb078863
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

Loading…