Carbon Dioxide → HCID 117720084, 화합물

HRID 1854586

반응식

HRID 1854586 반응식
C([N-]C(C)C)(C)C.[Li+].[CH3:9]N1CCCN(C)C1=O.[Cl:18][C:19]1[C:20]([CH3:27])=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23].[C:28](=[O:30])=[O:29].[OH-].[Na+]>O.O1CCCC1>[CH3:9][CH:27]([C:20]1[C:21]([C:22]#[N:23])=[CH:24][CH:25]=[CH:26][C:19]=1[Cl:18])[C:28]([OH:30])=[O:29]

참가 물질

8

반응물 5

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 5215083-Chloro-2-methylbenzonitrileHCID 2724682Lithium diisopropylamide

생성물 1

HCID 117720084HCID 117720084, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Add a 2M solution of lithium diisopropylamide in tetrahydrofuran (62.6 mL, 461.8 mmol) to tetrahydrofuran (1 L) at −78° C. Slowly add 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (19.94 mL, 164.91 mmol) followed by drop-wise addition of 3-chloro-2-methyl-benzonitrile (20 g, 131.93 mmol). Maintain the mixture at −78° C. with stirring for 5 min. Purge the reaction vessel with carbon dioxide (1 L; 25.65 moles) for 15 min. Add water (100 mL) and stir for 2 hr. Add 10M aqueous solution of sodium hydroxide to increase the pH of the aqueous phase to >12. Separate the aqueous layer and wash with diethyl ether. Acidify the aqueous layer with concentrated hydrochloric acid to pH-1 and extract with ethyl acetate. Separate the organic phase and dry over sodium sulfate. Filter and concentrate to dryness to yield the title compound as an off white solid (16.0 g; 81.80 mmol). MS (m/z): 195.9 (M+1).

후처리

  1. temperatureto increase the pH of the aqueous phase to >12
  2. customSeparate the aqueous layer
  3. washwash with diethyl ether
  4. extractionextract with ethyl acetate
  5. customSeparate the organic phase
  6. dry with materialdry over sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate to dryness

출처 및 근거

ORD 기록
ord-b07bdaf260d248c89b26f14d1a820c65
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962654B2

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