Tetrahydrofuran → HCID 67175351, compound

HRID 877855Notes

Reaction equation

HRID 877855 reaction equation
C([Li])CCC.Br.[CH2:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17])[CH3:8].[CH2:18]([N:20]([C:29]#[N:30])[C:21]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:28])[CH3:19].C1COCC1>CCCCCC>[CH3:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=1[N:9]([CH2:7][CH3:8])[C:29]([N:20]([C:21]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:28])[CH2:18][CH3:19])=[NH:30]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 67175497HCID 67175497, compoundHCID 87298019HCID 87298019, compoundHCID 178418339Butyllithium

Product 1

HCID 67175351HCID 67175351, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

n-Butyllithium (20.5 mL, 1.6 M in hexane, 32.8 mmol) was added dropwise to a stirred suspension of N-ethyl-2,6-dimethylaniline hydrobromide (3.8 g, 16.5 mmol) in hexane (40 mL) at 0° C. The reaction mixture was stirred for 1 h at room temperature and cooled subsequently to −80° C. N-Ethyl-N-cyano-2,6-dimethylaniline (2.92 g, 16.8 mmol) was added drop wise at −80° C. after which the reaction mixture was allowed to slowly warm up to room temperature. The resulting reaction mixture was stirred for 2 h at room temperature, during which hexane (60 mL) and THF (20 mL) were added to form a homogeneous solution. The reaction mixture was quenched and washed with water (100 mL). The organic layer was separated, the aqueous layer was extracted with diethyl ether (100 mL) and the combined organic layers were dried with Na2SO4. Filtration and rotatory evaporation of the volatiles yielded the desired guanidine as a yellow waxy material. Yield: 5.3 g (99%).

Workup

  1. temperaturecooled subsequently to −80° C
  2. temperatureto slowly warm up to room temperature
  3. customThe resulting reaction mixture
  4. additionwere added
  5. customto form a homogeneous solution
  6. customThe reaction mixture was quenched
  7. washwashed with water (100 mL)
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with diethyl ether (100 mL)
  10. dry with materialthe combined organic layers were dried with Na2SO4
  11. filtrationFiltration and rotatory evaporation of the volatiles

Sources & evidence

ORD record
ord-765dac251cea4adfa5e92dee84139b48
Source dataset
uspto-grants-2015_03
Patent number
US08987393B2

Reaction notes

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