Carbon Dioxide → HCID 117720084, compound

HRID 1854586

Reaction equation

HRID 1854586 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

HCID 117720084HCID 117720084, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b07bdaf260d248c89b26f14d1a820c65
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Linked notes

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