Pyridine → HCID 59226938, 화합물

HRID 1943118노트

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HRID 1943118 반응식
[NH2:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH3:18][C:19]1[CH:25]=[C:24]([C:26]([F:35])([C:31]([F:34])([F:33])[F:32])[C:27]([F:30])([F:29])[F:28])[CH:23]=[C:22]([CH3:36])[C:20]=1[NH2:21].N1C=CC=CC=1>ClCCl>[NH2:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([NH:21][C:20]1[C:22]([CH3:36])=[CH:23][C:24]([C:26]([F:35])([C:27]([F:28])([F:29])[F:30])[C:31]([F:32])([F:33])[F:34])=[CH:25][C:19]=1[CH3:18])=[O:7]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 27359463-Amino-2,4,5-trifluorobenzoic acidHCID 98824254-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2,6-dimethylaniline

생성물 1

HCID 59226938HCID 59226938, 화합물수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-Amino-2,4,5-trifluoro-benzoic acid (commerically available) (12.5 g, 65.50 mmol) was heated with thionyl chloride (110 ml) at 90° C. for 2 hours under a nitrogen atmosphere. The excess thionyl chloride was removed in vacuo. To a solution of the residue (13.37 g, 52.30 mmol) in dichloromethane (218 ml) under a nitrogen atmosphere was added a solution of 2,6-dimethyl-4-(heptafluoroprop-2-yl)aniline (prepared according to EP 1,006,102) (15.12 g, 52.30 mmol) in pyridine (4.2 ml, 52.30 mmol). The reaction mixture was stirred at ambient temperature for 2 hours and then extracted with aqueous hydrochloric acid (1M). The aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with aqueous sodium hydrogen carbonate (1M), dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3) to give 3-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,4,5-trifluoro-benzamide (18.4 g, 76% yield). 1H-NMR (400 MHz, CDCl3): 2.35 (6H, s), 4.07 (2H, bs), 7.3-7.35 (1H, m), 7.36 (2H, s), 7.83 (1H, d) ppm.

후처리

  1. customThe excess thionyl chloride was removed in vacuo
  2. extractionextracted with aqueous hydrochloric acid (1M)
  3. extractionThe aqueous phase was extracted twice with dichloromethane
  4. washThe combined organic phases were washed with aqueous sodium hydrogen carbonate (1M)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3)

출처 및 근거

ORD 기록
ord-b7939ef748ec40eb8fcea38aaca8d6a3
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389766B2

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