Methyl iodide → HCID 5282538, compound

HRID 1611012Notes

Reaction equation

HRID 1611012 reaction equation
[O-]CC.[Na+].[C:5]([NH:8][C:9](=[O:36])[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11]1[S:12][C:13]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:14][C:15]=1[C:16]([O:18]CC)=O)(=O)C.IC>C(O)C>[CH3:5][N:8]1[C:16](=[O:18])[C:15]2[CH:14]=[C:13]([CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[S:12][C:11]=2[N:10]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:9]1=[O:36]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 2723922Sodium ethoxideHCID 5282537HCID 5282537, compound

Product 1

HCID 5282538HCID 5282538, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (0.18 g) was added to a stirred solution of N′-acetyl-N-(2-methylpropyl)-N-[3-ethoxycarbonyl-5-(1-naphthalenylmethyl)-2-thienyl]urea (Example 3, step c), 0.30 g) in ethanol (6 ml). After 6 hours, iodomethane (0.165 ml) was added. After a further 16 hours iodomethane (0.165 ml) was added, After a further 24 hours, the reaction mixture was poured onto hydrochloric acid (2M, 30 ml) and extracted with ethyl acetate (2×30 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ether:hexane (1:1) and then triturated with ether to give the title compound (0.24 g).

Workup

  1. additionthe reaction mixture was poured onto hydrochloric acid (2M, 30 ml)
  2. extractionextracted with ethyl acetate (2×30 ml)
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica
  7. washeluting with ether:hexane (1:1)
  8. customtriturated with ether

Sources & evidence

ORD record
ord-a5698c0fba6d4f6eb1e73434f6f774f7
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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