Toluene → HCID 89499313, compound

HRID 336611Notes

Reaction equation

HRID 336611 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[CH2:11][N:12]1[CH:16]=[CH:15][CH:14]=[N:13]1)[CH2:8]2.[C:17]1(C)C=CC=CC=1.C([Li])CCC.CI>O1CCCC1>[CH3:17][C:16]1[N:12]([CH2:11][CH:2]2[CH:1]3[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]2[CH2:4]4)[CH2:8]3)[N:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 86681270HCID 86681270, compoundHCID 178418339Butyllithium

Product 1

HCID 89499313HCID 89499313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 62A (0.192 g, 0.888 mmol) in tetrahydrofuran (1 mL)/toluene (1 mL) was added n-butyllithium (1.6 M, 0.721 mL) at 0° C. The reaction mixture was stirred for 60 minutes. Then CH3I (0.166 mL) was added and stirring continued for 3 hours at 0° C. The reaction mixture was quenched with water, extracted with diethyl ether, dried over Na2SO4, filtered, and concentrated.

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours at 0° C
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with diethyl ether
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1a68f8d313314dad95a652d40c75a5bd
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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