Thionyl Chloride → 3-Bromo-5-chloro-N-cyclopropyl-4-methylbenzamide

HRID 1272720노트

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HRID 1272720 반응식
BrC1C=C(C=C(Cl)C=1C)C(O)=O.S(Cl)(Cl)=O.[Br:17][C:18]1[CH:19]=[C:20]([CH:27]=[C:28]([Cl:31])[C:29]=1[CH3:30])[C:21]([NH:23][CH:24]1[CH2:26][CH2:25]1)=[O:22].ClC1C=C(C=CC=1C)C(NC1CC1)=O>>[Br:17][C:18]1[CH:19]=[C:20]([CH:27]=[C:28]([Cl:31])[C:29]=1[CH3:30])[C:21]([NH:23][CH:24]1[CH2:26][CH2:25]1)=[O:22]

참가 물질

4

반응물 3

HCID 24386Thionyl ChlorideHCID 18457795515135-60-12회HCID 86760487HCID 86760487, 화합물

생성물 1

HCID 184577963-Bromo-5-chloro-N-cyclopropyl-4-methylbenzamide

반응 조건

온도
90 °C

실험 절차

3-Bromo-5-chloro-4-methylbenzoic acid (Intermediate 17, 310 mg, contaminated with 3-bromo-5-chloro-4-methylbenzoic acid) was mixed with thionyl chloride (3 ml) and the mixture heated at 90° C. for 2.5 hours. The excess thionyl chloride was evaporated under vacuum and the residue was dissolved in DCM (7.5 ml). Cyclopropylamine (0.2 ml) and sodium carbonate (500 mg) were added to the solution and the reaction stirred for 2 hours at room temperature. The reaction was filtered, the filtrate absorbed onto silica and applied to a SPE (Si, 10 g). The SPE was eluted with an ethyl acetate/cyclohexane gradient (p50% ethyl acetate) and the product fractions reduced to dryness under vacuum to give a mixture of 3-bromo-5-chloro-N-cyclopropyl-4-methylbenzamide/3-chloro-N-cyclopropyl-4-methylbenzamide (2:1).

후처리

  1. customThe excess thionyl chloride was evaporated under vacuum
  2. dissolutionthe residue was dissolved in DCM (7.5 ml)
  3. additionCyclopropylamine (0.2 ml) and sodium carbonate (500 mg) were added to the solution
  4. filtrationThe reaction was filtered
  5. customthe filtrate absorbed onto silica
  6. washThe SPE was eluted with an ethyl acetate/cyclohexane gradient (p50% ethyl acetate)
  7. customto give

출처 및 근거

ORD 기록
ord-6bf67fdb7750420e86f02f258fb4aa52
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208629B2

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