4-Methoxybenzylamine → HCID 117840111, compound

HRID 1477670Notes

Reaction equation

HRID 1477670 reaction equation
[N:1]1([C:6]([NH:8][C:9]([S:11][CH3:12])=[NH:10])=[O:7])[CH:5]=[CH:4]N=[CH:2]1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21]C(CN)=[CH:17][CH:16]=1>O1CCCC1>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:4]([CH2:5][N:1]2[CH:2]=[N:10][C:9]([S:11][CH3:12])=[N:8][C:6]2=[O:7])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 140668416HCID 140668416, compound

Product 1

HCID 117840111HCID 117840111, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution (5.0 mL) of methyl 1H-imidazole-1-carbonylcarbamimidothioate (921 mg, 5.00 mmol) synthesized in Reference Synthesis Example 289 was refluxed and a tetrahydrofuran solution (5.0 mL) of 4-methoxybenzylamine (343 mg, 2.50 mmol) was added dropwise to the refluxed solution, followed by refluxing the resultant mixture for 30 minutes. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain a compound. The obtained compound was used to obtain the title compound (355 mg, two step yield 48%) by synthesis in a similar manner to Reference Synthesis Example 291.

Workup

  1. temperaturewas refluxed
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  5. customto obtain a compound

Sources & evidence

ORD record
ord-b4976e8bdf34408087a6ea14bbbd2cd7
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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