Diisopropylamine → HCID 11346171, compound

HRID 2216922Notes

Reaction equation

HRID 2216922 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15](=[O:35])[N:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](=[O:34])N(C)C)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]>C1COCC1.CCCCCC>[CH3:13][O:14][C:15]([N:16]1[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30](=[O:34])[CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]1=2)=[O:35]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 11347480HCID 11347480, compoundHCID 178418339Butyllithium

Product 1

HCID 11346171HCID 11346171, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

Diisopropylamine (11.66 g, 0.115 mol, 1.2 eq.) is dissolved in THF (150 mL) and the solution is cooled down to −10° C. A solution of n-Butyllithium in hexane (72 mL of a 1.6 M solution, 1.2 eq.) is added slowly in order to keep the temperature below 0° C. (40 min). A solution of (2-dimethylcarbamoyl-phenyl)-o-tolyl-carbamic acid methyl ester (30.2 g, 0.096 mol, 1 eq.) in THF (80 mL) is added in 45 min. to the obtained solution. The reaction mixture is stirred for 1 hour at −5° C. before quenching by addition of water (30 mL). The mixture is concentrated in vacuum and water (220 mL) and ethylacetate (220 mL) are added to the oily residue. The phases are stirred rapidly before letting them separate. The organic phase is washed with aqueous sulfuric acid (300 mL of 1-M solution) and twice with water (300 mL). The organic phase is evaporated to dryness and delivers 23.0 g (89.5% yield) of the title compound as an orange oil that solidifies on standing.

Workup

  1. customthe temperature below 0° C. (40 min)
  2. custombefore quenching by addition of water (30 mL)
  3. concentrationThe mixture is concentrated in vacuum and water (220 mL) and ethylacetate (220 mL)
  4. additionare added to the oily residue
  5. stirringThe phases are stirred rapidly
  6. customseparate
  7. washThe organic phase is washed with aqueous sulfuric acid (300 mL of 1-M solution) and twice with water (300 mL)
  8. customThe organic phase is evaporated to dryness

Sources & evidence

ORD record
ord-e963ca3dd27b417787b8b95631cdb210
Source dataset
uspto-grants-2006_09
Patent number
US07112673B2

Reaction notes

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