Hydrochloric Acid → 2-Mercaptobenzophenone

HRID 583479Notes

Reaction equation

HRID 583479 reaction equation
CN(C)CCN(C)C.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([Li])CCC.CON(C)[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>C1CCCCC1>[SH:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 569575N-Methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 34997132-MercaptobenzophenoneYield 59.6%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To a solution of N,N,N',N'-tetramethylethylene diamine (4.4 g, 0.038 mol) and thiophenol (2 g, 0.018 mol) in cyclohexane (40 mL) was added dropwise n-butyllithium (24 mL, 0.038 mol) at room temperature. The suspension was stirred under nitrogen for 16 hours, followed by the dropwise addition of N-methoxy-N-methylbenzamide (3.3 g, 0.019 mol). After stirring for 20 minutes, the reaction mixture was added to cold aqueous HCl (1N). The product was partitioned between ethyl acetate and the acidic solution. The layers were separated and the organic portion was washed with brine, dried (Na2SO4), filtered, and the filtrate was concentrated in vacuo. The liquid obtained was purified using silica gel chromatography (75% hexane/25% ethyl acetate) to give 2.3 g of the title compound a as a viscous yellow liquid.

Workup

  1. stirringAfter stirring for 20 minutes
  2. customThe product was partitioned between ethyl acetate
  3. customThe layers were separated
  4. washthe organic portion was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe liquid obtained
  9. customwas purified

Sources & evidence

ORD record
ord-bad8cd9071f84508ac287e6834e7f2ea
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Reaction notes

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