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

HRID 1272720ノート

反応式

HRID 1272720 の反応式
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]

参加物

4

反応物 3

HCID 24386Thionyl ChlorideHCID 18457795515135-60-12 回HCID 86760487HCID 86760487、化合物

生成物 1

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

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6bf67fdb7750420e86f02f258fb4aa52
出典データセット
uspto-grants-2007_04
特許番号
US07208629B2

反応ノート

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