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

HRID 450357
ノート
印刷プレビュー

反応式

HRID 450357 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-156371ae87874334ad1ee55980d57698
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486966B2

反応ノート

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