Diisobutylamine → HCID 68448515, compound

HRID 1516759Notes

Reaction equation

HRID 1516759 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=O)[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13].C(N(C(C)C)CC)(C)C.[CH2:30]([NH:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:31]([CH3:33])[CH3:32]>ClCCl>[Cl:5][C:6]1[CH:7]=[C:8]([C:15]([CH3:20])([CH3:19])[C:16]([N:34]([CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:18])[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 8085DiisobutylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 68448777HCID 68448777, compound

Product 1

HCID 68448515HCID 68448515, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (0.54 ml, 4 eq) is added to a solution of 2-(3-chloro-4-nitrophenyl)-2-methylpropanoic acid (500 mg) in dichloromethane (1 ml). The mixture is heated under reflux for 16 hours then cooled down to ambient temperature. The solvent is evaporated off under reduced pressure at 40° C. (co-evaporation with toluene). Diisopropylethylamine (0.42 ml, 1.2 eq) and the diisobutylamine (0.36 ml, 1 eq) are successively added to a solution of the acid chloride thus obtained in dichloromethane (1 ml), cooled down to 0° C. At the end of the addition, stirring is continued for 3 hours at ambient temperature then the mixture is concentrated under reduced pressure at 40° C. The residue is dissolved in ethyl ether and the organic phase is washed successively with 1N soda, a saturated sodium hydrogen carbonate solution, salt water than dried over Na2SO4 and concentrated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2 to 7:3) produces the expected compound in the form of an oil which crystallizes (0.585 g; 82% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. customThe solvent is evaporated off under reduced pressure at 40° C. (co-evaporation with toluene)
  4. temperaturecooled down to 0° C
  5. additionAt the end of the addition
  6. concentrationthe mixture is concentrated under reduced pressure at 40° C
  7. dissolutionThe residue is dissolved in ethyl ether
  8. washthe organic phase is washed successively with 1N soda
  9. dry with materiala saturated sodium hydrogen carbonate solution, salt water than dried over Na2SO4
  10. concentrationconcentrated under reduced pressure at 40° C
  11. customPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2 to 7:3)

Sources & evidence

ORD record
ord-c9c43269908e470eb3cf4f8091a60314
Source dataset
uspto-grants-2012_07
Patent number
US08227485B2

Reaction notes

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