Carbon Dioxide → HCID 59355403, compound

HRID 887710Notes

Reaction equation

HRID 887710 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[Cl:14])([CH3:4])([CH3:3])[CH3:2].[C:16](=[O:18])=[O:17].CC(C)=O.C([Li])CCC.C(=O)=O.[OH-].[Na+]>C(OCC)C.O>[C:1]([O:5][C:6]([NH:7][C:8]1[C:13]([C:16]([OH:18])=[O:17])=[CH:12][N:11]=[CH:10][C:9]=1[Cl:14])=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 18522661Acetone cardiceHCID 45789215HCID 45789215, compoundHCID 178418339Butyllithium

Product 1

HCID 59355403HCID 59355403, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-10 °C

Procedure

(3-Chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (1.50 g) was dissolved in dry diethyl ether (35 mL), N,N,N′,N′-tertamethylenethylendiamine (2.35 mL) was added and the reaction mixture was cooled in a dry ice/acetone cool bath to −78° C. n-Butyl lithium (9.9 mL, 1.59M in hexane) was added to the suspension, the cool bath was replaced by a sodium chloride/ice mixture and the reaction mixture was stirred at −10° C. for 1.5 h. The suspension was slowly poured on crushed dry ice (2.0 g) in dry diethyl ether (20 mL) and stirred for 1 h. Water was added and the pH was adjusted to −12 by addition of 2N sodium hydroxide solution. The aqueous layer was washed 2× with MTB-ether, 2 M hydrochloric acid was added to the aqueous layer and the pH was adjusted to −2 and the aqueous layer was 3× extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum to afford 1.03 g of the title compound of the formula

Workup

  1. additionN,N,N′,N′-tertamethylenethylendiamine (2.35 mL) was added
  2. additionwas added to the suspension
  3. additionThe suspension was slowly poured
  4. stirringstirred for 1 h
  5. washThe aqueous layer was washed 2× with MTB-ether, 2 M hydrochloric acid
  6. additionwas added to the aqueous layer
  7. extractionextracted with ethyl acetate
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-6525a3abe87b4d7a9c882a6d2492376c
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

Loading…