Methyl iodide → HCID 178503594, compound

HRID 1471850Notes

Reaction equation

HRID 1471850 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH:5]=[CH:6][CH:7]=1.O([C:19](C)(C)C)[K].[C:23](=[S:25])=S.IC.O.[NH2:29][NH2:30]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:29][NH:30][C:19]=2[S:25][CH3:23])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24654Hydrazine hydrate (1:1)HCID 2466012-(3-chlorophenyl)-1-phenylethanoneHCID 178418922HCID 178418922, compound

Product 1

HCID 178503594HCID 178503594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3-chlorophenyl)-1-phenylethanone (5 g, 21.67 mmol) in anhydrous THF (10 mL) was added a solution of 1.0 M KO-t-Bu in THF. The reaction was stirred for 15 min at room temperature, then CS2 (1382 g, 23.41 mmol) was added. After 10 min, iodomethane (6.77 g, 47.7 mmol) was added and the reaction was stirred for 4 h. The reaction was washed with saturated NaHCO3 solution and dried over MgSO4. The filtrate was concentrated under reduced pressure and the residue was triturated with 10% ethyl acetate. The solid was suspended in ethanol and hydrazine hydrate (5.43 g, 108 mmol) was added at room temperature. The reaction was refluxed for 4 h. The reaction mixture was concentrated under reduced pressure and the residue was triturated with ethyl acetate/hexane to give the title compound as a white solid (4.9 g). LCMS m/z=301.1 [M+H]+.

Workup

  1. waitAfter 10 min
  2. stirringthe reaction was stirred for 4 h
  3. washThe reaction was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was triturated with 10% ethyl acetate
  7. temperatureThe reaction was refluxed for 4 h
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customthe residue was triturated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-4ca0323c86014e88a00adfb7d24c29ae
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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