Dimethylformamide → HCID 15052590, compound

HRID 129677Notes

Reaction equation

HRID 129677 reaction equation
[H-].[Na+].CN(C=O)C.[C:8]12([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=3[OH:28])[C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[CH3:29][N:30]([CH3:34])[C:31](Cl)=[S:32]>O>[C:8]12([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=3[O:28][C:31]([N:30]([CH3:34])[CH3:29])=[S:32])[C:21]([O:23][CH3:24])=[O:22])[CH2:9][CH:10]3[CH2:16][CH:14]([CH2:13][CH:12]([CH2:11]3)[CH2:17]1)[CH2:15]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 14852531HCID 14852531, compound

Product 1

HCID 15052590HCID 15052590, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a round bottom flask, there are introduced 2.4 g (0.08 mole) of sodium hydride (80% in oil) and 250 ml of DMF. Under a nitrogen current, there are slowly added 22.9 g (0.08 g mole) of methyl 3-(1-adamantyl)-4-hydroxybenzoate. The mixture is stirred until the cessation of gaseous emission. There are then added, all at once, 12.9 g (0.104 mole) of dimethylthiocarbamoyl chloride and the mixture is stirred for 16 hours at ambient temperature. The reaction medium is poured into water and extracted with ethyl ether. The organic phase is decanted, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column eluted with a 70:30 mixture of dichloromethane and hexane. After evaporation of the solvents, 1.8 g (63% yield) of the expected product having a melting point of 174°-175° C. are recovered.

Workup

  1. additionThere are then added
  2. extractionextracted with ethyl ether
  3. customThe organic phase is decanted
  4. customdried on magnesium sulfate
  5. customevaporated
  6. customThe resulting residue is purified by chromatography on a silica column
  7. washeluted with a 70:30 mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-eb9864fd7f6146ac9391a36a41dc531e
Source dataset
uspto-grants-1995_11
Patent number
US05468897

Reaction notes

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