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Dimethylformamide → 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide

HRID 1522785
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HRID 1522785 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[S:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[N:29](C)C=O.C(Cl)(=O)C(Cl)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[S:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:29])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
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참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 894445434-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acid

생성물 1

HCID 894445764-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acid (1.65 g) was suspended in dichloromethane (16 mL). A catalytic amount of N,N-dimethylformamide (“DMF”) and oxalyl chloride (1.2 eq.) were added to the suspension. The reaction mixture was stirred at ambient temperature for 1.5 hour. The reaction mixture was concentrated and the residue dissolved in dry tetrahydrofuran (16 mL). To the solution was added a solution of ammonium hydroxide (8 mL, 25%). The reaction mixture was stirred at ambient temperature for two hours. It was then quenched by addition of water and extracted with ethyl acetate. The organic extract was washed with a saturated solution of sodium hydrogenocarbonate, dried over magnesium sulfate and concentrated in vacuo. The crude residue was triturated with tert-butylmethylether then the precipitate was filtered and dried under vacuo to give the title compound (841 mg) as a solid. 1H-NMR (CDCl3, 400 MHz): δ=7.50-7.61 (m, 2 H), 7.39-7.50 (m, 1 H), 7.29-7.39 (m, 1 H), 7.14-7.27 (m, 2 H), 6.40 (br. s., 1 H), 6.05 (br. s., 1 H), 4.16 (m, J=17.4, 1 H), 3.74-3.91 (m, 1 H), 2.44-2.49 (m, 3 H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in dry tetrahydrofuran (16 mL)
  3. additionTo the solution was added a solution of ammonium hydroxide (8 mL, 25%)
  4. stirringThe reaction mixture was stirred at ambient temperature for two hours
  5. customIt was then quenched by addition of water
  6. extractionextracted with ethyl acetate
  7. extractionThe organic extract
  8. washwas washed with a saturated solution of sodium hydrogenocarbonate
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was triturated with tert-butylmethylether
  12. filtrationthe precipitate was filtered
  13. customdried under vacuo

출처 및 근거

ORD 기록
ord-f001d53ecba541939357d916545ac91a
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09078444B2

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