Hydrochloric Acid → HCID 19068250, compound

HRID 1957688Notes

Reaction equation

HRID 1957688 reaction equation
[H-].[Na+].[SH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[C:14]12([C:24]3[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=3[O:32][CH3:33])[CH2:27]Br)[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.Cl>CN(C=O)C.O>[C:14]12([C:24]3[CH:25]=[C:26]([CH2:27][S:3][C:4]4[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=4)[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:22]3)[CH2:21]1)[CH2:23]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19068276HCID 19068276, compound

Product 1

HCID 19068250HCID 19068250, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

1.44 g (48 mmol) of sodium hydride (80% in oil) and 25 ml of DMF were introduced into a three-necked flask under a stream of nitrogen. A solution of 6.73 g (40 mmol) of methyl 4-mercaptobenzoate in 60 ml of DMF was added dropwise and the mixture was stirred until the evolution of gas had ceased. A solution of 16.1 g (48 mmol) of 3-(1-adamantyl)-4-methoxybenzyl bromide in 90 ml of DMF was then added and the mixture was stirred at room temperature for eight hours. The reaction medium was poured into water, acidified to pH 1 with hydrochloric acid and extracted with ethyl ether. 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 (40/60). After evaporation of the solvents, 16.75 g (99%) of the expected methyl ester, having a melting point of 143°-5° C., were recovered.

Workup

  1. stirringthe mixture was stirred at room temperature for eight hours
  2. extractionextracted with ethyl ether
  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 (40/60)
  10. customAfter evaporation of the solvents, 16.75 g (99%) of the expected methyl ester
  11. customwere recovered

Sources & evidence

ORD record
ord-da85199ced2f496b85742323572514e3
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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