Methyl iodide → HCID 14625407, compound

HRID 2107815Notes

Reaction equation

HRID 2107815 reaction equation
[C:1]1([N:7]2[CH2:22][CH2:21][N:11]3[C:12]4[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=4[NH:14][C:15](=[S:16])[N:10]3[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23]C(C)([O-])C.[K+].CI>CN(C)C=O>[CH3:23][S:16][C:15]1[N:10]2[CH2:9][CH2:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:22][CH2:21][N:11]2[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14625406HCID 14625406, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14625407HCID 14625407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,3,4,5-tetrahydro-3-phenyl-1H-[1,2,5]triazepino[1,2-a][1,2,4]benzotriazine-7(8H)-thione (3.1 g from Example 12) and potassium t-butoxide (1.29 g) in N,N-dimethylformamide (50 ml, dried over 4A molecular sieves) was added methyl iodide (2 ml) and the reaction flask was sealed rapidly. An exothermic reaction ensued. The solution was left at room temperature overnight. The solution was evaporated and the residue was extracted with chloroform. The extract was applied to a column (71×3.2 cm) of dry column grade neutral alumina prepacked in chloroform. Elution with chloroform furnished a major component. Appropriate fractions were evaporated to a syrup. Trituration with heptane gave crude titled product; wt. 2.21 g, (65%), mp=125°-127°. Recrystallization (with decolorization) from dichloromethane-heptane furnished pure product; mp=128°-130°, m/e (E.I.) 324; maxKBr 1589, 765, 748, 693 cm-1 ; pmr (100 MHz, DMSO-D6) 2.42 (3H, singlet), 3.29 (2H, triplet, J=6 Hz), 3.67 (2H, triplet, J=6 Hz), 3.81 (2H, triplet, J=6 Hz), 3.89 (2H, triplet, J=6 Hz), 6.64-7.34 (9H, overlapping multiplets).

Workup

  1. customthe reaction flask was sealed rapidly
  2. customAn exothermic reaction
  3. customThe solution was evaporated
  4. extractionthe residue was extracted with chloroform
  5. washElution with chloroform
  6. customfurnished a major component
  7. customAppropriate fractions were evaporated to a syrup

Sources & evidence

ORD record
ord-884cece1b07846bfa96bf2ae53577fc6
Source dataset
uspto-grants-1990_06
Patent number
US04935515

Reaction notes

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