Dimethylformamide → 2-Chlorocyclohex-1-ene-1-carbonitrile

HRID 215743

반응식

HRID 215743 반응식
O=P(Cl)(Cl)Cl.C[N:7]([CH:9]=O)C.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[ClH:18].NO>O>[Cl:18][C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[C:9]#[N:7]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7967CyclohexanoneHCID 24813Phosphorus oxychlorideHCID 443297Hydroxyamine hydrochloride

생성물 1

HCID 498409392-Chlorocyclohex-1-ene-1-carbonitrile수율 60.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

To a stirring solution of POCl3 (15.20 mL, 163 mmol) at 0° C. was added DMF (13.40 mL, 173 mmol) drop-wise. Monitoring internal temperature, cyclohexanone (10.60 mL, 102 mmol) was slowly added, keeping the temperature between 35 and 40° C. Upon complete addition, the reaction was heated to 50° C. and hydroxylamine hydrochloride (40 g, 576 mmol) was added in eight portions, cooling when necessary to control the exothermic reaction. Upon completing this addition, ice was added to the reaction, followed by water (400 mL), and the mixture resumed stirring for 1 h. Filtration afforded the desired product as a brown solid (8.8 g). Some substrates may require an aqueous work-up/extraction procedure if water solubility is too high. EtOAc is generally a good solvent for this extraction. MS: No signal. 1H NMR (400 MHz, CDCl3 δ ppm 2.47-2.36 (m, 2H), 2.34-2.25 (m, 2H), 1.78-1.67 (m, 1H), 1.67-1.58 (m, 1H).

후처리

  1. customthe temperature between 35 and 40° C
  2. additionUpon complete addition
  3. temperaturecooling when necessary
  4. customthe exothermic reaction
  5. additionthis addition, ice
  6. additionwas added to the reaction
  7. filtrationFiltration

출처 및 근거

ORD 기록
ord-3ed87f4794ce40e882f23c7064c7d2c7
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193178B2

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