Methyl iodide → HCID 67165187, compound

HRID 552375Notes

Reaction equation

HRID 552375 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:19])[N:7]([CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:8](=[O:14])[NH:9]2)([O-:3])=[O:2].[C:20]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:19])[N:7]([CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:8](=[O:14])[N:9]2[CH3:20])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67166860HCID 67166860, compound

Product 1

HCID 67165187HCID 67165187, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Step 2 intermediate (5 g, 19.15 mmol) in dry DMF (56 ml) was added anhydrous K2CO3 (3.17 g, 22.98 mmol) and the mixture was stirred at room temperature for 30 min. Methyl iodide (1.43 ml, 22.98 mmol) was added drop-wise and the mixture was further stirred at room temperature for 24 h. The reaction mixture was diluted with water (100 ml) and the solid precipitated out was filtered and washed with water and dried to give 5.5 g of the product as off white solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz): 7.90 (t, J=7.8, 1H); 7.66 (d, J=8.7, 1H); 7.55 (d, J=7.8, 1H); 3.76 (d, J=7.2, 2H); 3.55 (s, 3H); 1.20-1.10 (m, 1H); 0.47-0.40 (m, 2H); 0.35-0.28 (m, 2H).

Workup

  1. stirringthe mixture was further stirred at room temperature for 24 h
  2. customthe solid precipitated out
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-56d7fb545b814702a3816a979e76e642
Source dataset
uspto-grants-2011_05
Patent number
US07951814B2

Reaction notes

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