Triethylamine → Methyl 4-(2,3,4-trimethoxybenzoyl)-1-piperazinecarbodithioate

HRID 1460193

반응식

HRID 1460193 반응식
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.[N:20]1([C:26]([S:28][CH3:29])=[S:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>ClCCl>[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:8]=1[C:9]([N:23]1[CH2:24][CH2:25][N:20]([C:26]([S:28][CH3:29])=[S:27])[CH2:21][CH2:22]1)=[O:11]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 113082,3,4-Trimethoxybenzoic acidHCID 24386Thionyl ChlorideHCID 21278808Methyl piperazine-1-carbodithioate

생성물 1

HCID 19388490Methyl 4-(2,3,4-trimethoxybenzoyl)-1-piperazinecarbodithioate수율 51.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a nitrogen atmosphere, 10 ml (138 mmol.) of thionyl chloride was added to 1.00 g (4.71 mmol.) of 2,3,4-trimethoxybenzoic acid. The mixture was refluxed under heating for 2 hours. The solvent was distilled off under reduced pressure. To the residue was added 10 ml of dry benzene, and the mixture was placed under reduced pressure to distill off benzene. This procedure was repeated once. To the residue was dropwise added at room temperature a solution of 0.88 g (4.74 mmol., purity 95%) of methyl 1-piperazinecarbodithioate in 12 ml of dichloromethane. In the course of the addition, 0.48 g (4.74 mmol.) of triethylamine was added to the mixture. The resulting mixture was then stirred overnight. The reaction mixture was washed successively with 1-N hydrochloric acid and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and placed under pressure to distill off the solvent. The residue was crystallized from acetone. The crystals were collected by filtration. The filtrate was concentrated, and additional crystals were further precipitated from the concentrated filtrate by addition of a small amount of ethanol. These crystalline portions were combined to give 0.90 g of the desired compound as a white crystalline product, m.p. 149°-150° C. (decomp.), yield 51.6%.

후처리

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added 10 ml of dry benzene
  5. distillationto distill off benzene
  6. additionwas added to the mixture
  7. washThe reaction mixture was washed successively with 1-N hydrochloric acid
  8. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  9. distillationto distill off the solvent
  10. customThe residue was crystallized from acetone
  11. filtrationThe crystals were collected by filtration
  12. concentrationThe filtrate was concentrated
  13. customadditional crystals were further precipitated from the concentrated filtrate by addition of a small amount of ethanol

출처 및 근거

ORD 기록
ord-eb249bbefe74479fae360de952c3629f
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05070089

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