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

HRID 385125노트

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HRID 385125 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8ff2c5cde9514b808845ff208181ecd4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367843B2

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