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Triethylamine → 4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamide

HRID 2233582
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HRID 2233582 반응식
[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:35][OH:36].C(N(CC)CC)C>O1CCCC1.CO>[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]([NH:35][OH:36])=[NH:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:36])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59296163HCID 59296163, 화합물

생성물 2

HCID 866138984-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamideHCID 178441583HCID 178441583, 화합물

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 180 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzonitrile in 5 mL of tetrahydrofuran and 10 ml of methanol was added 267 mg of hydroxylamine hydrochloride followed by 0.55 mL of triethylamine. The resulting mixture was heated to 60° C. overnight. The solvents were removed in vacuo, the resulting residue was poured into water and extracted with ethylacetate. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 1/ethyl acetate 1) to give 90 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-N-hydroxy-2-trifluoromethyl-benzamidine and 50 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamide.

후처리

  1. customThe solvents were removed in vacuo
  2. additionthe resulting residue was poured into water
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (heptane 1/ethyl acetate 1)

출처 및 근거

ORD 기록
ord-722dc581849240309170170d5d7091d6
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709509B2

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