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Isopropanol → 5-Isopropoxy-1H-pyrazol-3-amine

HRID 450357
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HRID 450357 반응식
[NH2:1][C:2]1[CH:6]=[C:5]([OH:7])[NH:4][N:3]=1.[C:8]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:13]=CC=C[CH:9]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(O)(C)C>C(Cl)Cl>[CH:8]([O:7][C:5]1[NH:4][N:3]=[C:2]([NH2:1])[CH:6]=1)([CH3:13])[CH3:9]
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참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 962213-Amino-5-hydroxypyrazole

생성물 1

HCID 1784587215-Isopropoxy-1H-pyrazol-3-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

The title compound may be prepared via the following procedure: To a suspension of 3-amino-5-hydroxypyrazole (0.50 mol) in CH2Cl2 is added triphenylphosphine (0.59 mol) and the resulting mixture is cooled to 0° C. Diisopropyl azodicarboxylate (0.59 mol) is added drop-wise over a period of 35 minutes (the temperature of the reaction mixture is kept below 2° C.) to give a suspension. The reaction mixture is then held at 0° C. for 1 hour. A precipitate may be observed after 30 minutes of the reaction. Isopropyl alcohol (1.25 mol) is then added drop-wise over a period of 30 minutes at 0° C. as the slurry thins considerably to give a suspension. The reaction mixture is then held at 0° C. for 1 hour. The reaction mixture is warmed slowly to ambient temperature and is then held at ambient temperature overnight. The reaction mixture is filtered to remove undissolved solids. The filtrate is dried (MgSO4) and concentrated under reduced pressure to give an oil. Purification by column chromatography (5%→10% MeOH in CH2Cl2) affords the title compound. (400 MHz, DMSO-d6) δ ppm 10.3 (br s, 1H), 4.84 (br s, 2H), 4.65 (s, 1H), 4.52 (m, 1H), 1.20 (m, 6H).

후처리

  1. customis kept below 2° C.
  2. customto give a suspension
  3. customA precipitate may be observed after 30 minutes of the reaction
  4. customto give a suspension
  5. waitThe reaction mixture is then held at 0° C. for 1 hour
  6. temperatureThe reaction mixture is warmed slowly to ambient temperature
  7. waitis then held at ambient temperature overnight
  8. filtrationThe reaction mixture is filtered
  9. customto remove undissolved solids
  10. dry with materialThe filtrate is dried (MgSO4)
  11. concentrationconcentrated under reduced pressure
  12. customto give an oil
  13. customPurification by column chromatography (5%→10% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-156371ae87874334ad1ee55980d57698
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486966B2

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