Methyl iodide → HCID 9948559, compound

HRID 1385281Notes

Reaction equation

HRID 1385281 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:17][C:6]2=[C:7]([C:12]3[NH:16][N:15]=[N:14][N:13]=3)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:18])[CH2:3]1.[CH2:20](N(CC)CC)C.IC>CN(C=O)C.CCOC(C)=O.O>[CH3:1][C:2]1([CH3:19])[CH2:17][C:6]2=[C:7]([C:12]3[N:16]=[N:15][N:14]([CH3:20])[N:13]=3)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:18])[CH2:3]1

Participants

7

Reactant 3

HCID 6328Methyl iodide2×HCID 8471TriethylamineHCID 178503630HCID 178503630, compound

Product 1

HCID 9948559HCID 9948559, compoundYield 14.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To solution of 6,6-dimethyl-3-methylthio-1-(tetrazol-5-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (62 mg, 0.21 mmol) in DMF (5 mL) containing triethylamine (58 μL, 0.42 mmol) was added iodomethane (13 μL, 0.21 mmol). After stirring for 1 h more iodomethane (39 μL, 0.63 mmol) was added and stirring continued overnight. Ethyl acetate (20 ml) and water (20 mL) were added and the organic layer separated, dried (Na2SO4) and evaporated. The residue was triturated with CH2Cl2:EtOAc (1:1) and the undissolved solid (26 mg; 0.08 mmol) collected by filtration and washed with EtOAc. The filtrate was chromatographed on silica gel, eluting with petrol:EtOAc (2:) to give the title compound (10 mg, 0.03 mmol) as a tan solid. Total mass=36 mg (56%), mp 233-235° C. Found C, 50.26; H, 5.23; N, 17.94%. C13H16N4S2O requires: C,50.63; H, 5.23; N, 18.17%. 1HNMR (250 MHz, CDCl3) δ 1.10 (6H, s), 2.45 (2H, s), 2.65 (3H, s), 3.11 (2H, s), 4.40 (3H, s). MS (ES+) 309 (M+1).

Workup

  1. additionwas added
  2. customthe organic layer separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was triturated with CH2Cl2:EtOAc (1:1)
  6. filtrationthe undissolved solid (26 mg; 0.08 mmol) collected by filtration
  7. washwashed with EtOAc
  8. customThe filtrate was chromatographed on silica gel
  9. washeluting with petrol

Sources & evidence

ORD record
ord-2ef396b0b47849c0bfb82dd152e9f459
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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