Dimethylformamide → HCID 86709875, 화합물

HRID 541051노트

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HRID 541051 반응식
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]([OH:17])=O)[CH:3]=1.S(Cl)([Cl:20])=O.CN(C)C=O.CN(C1C=CC=CN=1)C>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]([Cl:20])=[O:17])[CH:3]=1

참가 물질

7

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HCID 6228DimethylformamideHCID 218852-DimethylaminopyridineHCID 24386Thionyl ChlorideHCID 86709876HCID 86709876, 화합물

생성물 1

HCID 86709875HCID 86709875, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매2회

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온도
80 °C

실험 절차

To a mixture of 4,5-dichloro-6-phenylpicolinic acid (3.00 g, 11.2 mmol) in toluene (40 mL) was added thionyl chloride (1.22 mL, 16.8 mmol) and dimethylformamide (0.04 mL, 0.6 mmol). Reaction mixture was heated at 80° C. for 3 h. HPLC analysis of an aliquot of the reaction mixture treated with methanol and dimethylaminopyridine indicated complete conversion of the starting material. Reaction was allowed to cool to room temperature and concentrated under reduced pressure to provide a white solid. Toluene (40 mL) was added to dissolve the solid and concentrated under reduced pressure and then this process was performed a second time. 4,5-Dichloro-6-phenylpicolinoyl chloride was isolated as a white solid (2.84 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 7.83-7.75 (m, 2H), 7.55-7.47 (m, 3H); 13C NMR (101 MHz, CDCl3) δ 168.80, 158.88, 146.42, 145.21, 136.79, 134.40, 129.98, 129.61, 128.31, 124.74; MS: Calcd. for C12H6Cl3NO: 284.95. Found: 285 (M+), 250, 222, 187, 152; mp=106-111° C.

후처리

  1. customReaction mixture
  2. customReaction
  3. temperatureto cool to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customto provide a white solid
  6. dissolutionto dissolve the solid
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-da3b9de786144261a9b1c9cb7ca9006a
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871943B2

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