Formaldehyde → 3-(3-Formyl-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

HRID 385125ノート

反応式

HRID 385125 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH2:2]1.NC1C=CC=CC=1S.C=O.C(N(C(C)C)CC)(C)C.[CH:29]([C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([C:42]([F:45])([F:44])[F:43])[C:39]=1[O:40][CH3:41])[C:34](Cl)=[O:35])=[O:30]>ClCCl>[CH:29]([C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([C:42]([F:43])([F:45])[F:44])[C:39]=1[O:40][CH3:41])[C:34]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:35])=[O:30]

参加物

7

反応物 5

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 81531DiisopropylethylamineHCID 96588BenzothiazolineHCID 866681783-Formyl-4-methoxy-5-trifluoromethylbenzoyl chloride

生成物 1

HCID 866681793-(3-Formyl-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (1.55 g) and 37% formalin (1.0 mL) in the same manner as in Example 1 was dissolved in dichloromethane (15 mL), and diisopropylethylamine (2.7 mL) and 3-formyl-4-methoxy-5-trifluoromethylbenzoyl chloride (2.42 g) were added to the solution, and then the mixture was stirred at room temperature for 14 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the title compound (1.44 g) as a yellow oily substance.

後処理

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-8ff2c5cde9514b808845ff208181ecd4
出典データセット
uspto-grants-2013_02
特許番号
US08367843B2

反応ノート

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