Methyl iodide → HCID 22461311, compound

HRID 1937628Notes

Reaction equation

HRID 1937628 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:10][C:9]2[NH:8][C:7]([S:11][C:12]#N)=[CH:6][C:5]=2[C:4](=[O:14])[CH2:3]1.CI.[OH-].[K+].CO.O>CO>[CH3:1][C:2]1([CH3:15])[CH2:10][C:9]2[NH:8][C:7]([S:11][CH3:12])=[CH:6][C:5]=2[C:4](=[O:14])[CH2:3]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 22242641Methanol--water (1/1)HCID 22461258HCID 22461258, compound

Product 1

HCID 22461311HCID 22461311, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6,6-dimethyl-2-thiocyanato-4,5,6,7-tetrahydro-1H-indol-4-one (400 mg, 1.8 mmol) and MeI (124 μL, 2.0 mmol) in MeOH (10 mL) at −5° C. was added a solution of KOH (117 mg, 2.1 mmol) in 1:1 MeOH/water (6 mL), maintaining the temperature below 0° C. The mixture was stirred for 3 h at room temperature, after which time the MeOH was removed and the residue partitioned between DCM and water. The organic layer was separated and the aqueous phase re-extracted with DCM. The combined organic layers were dried (Na2SO4) and evaporated to afford the title compound (350 mg, 88%) as a colourless solid. mp 195-196° C. Found: C, 62.20; H, 7.13; N, 6.34%. Calc. C11H15NOS.0.2(H2O): C, 62.06; H, 7.29; N, 6.58%. 1H NMR (360 MHz, d6-DMSO) δ 1.02 (6H,s), 2.19 (2H,s), 2.34 (3H,s), 2.61 (2H,s), 6.30 (1H,d, J=2.4 Hz), 11.59 (1H,br s). MS (ES+) 210 (M+1).

Workup

  1. temperaturemaintaining the temperature below 0° C
  2. customafter which time the MeOH was removed
  3. customthe residue partitioned between DCM and water
  4. customThe organic layer was separated
  5. extractionthe aqueous phase re-extracted with DCM
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-d8bead2021c440bf8fbe9a5d0f2f37a2
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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