Benzylamine → HCID 59351488, compound

HRID 1889315Notes

Reaction equation

HRID 1889315 reaction equation
[NH2:1][C:2]1[S:3][C:4]([O:13][CH3:14])=[C:5]([CH3:12])[C:6]=1[C:7]([O:9]CC)=O.ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:34]1([CH2:40][NH2:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH2:40]([N:41]1[C:7](=[O:9])[C:6]2[C:5]([CH3:12])=[C:4]([O:13][CH3:14])[S:3][C:2]=2[NH:1][C:19]1=[O:25])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 15892483HCID 15892483, compound

Product 1

HCID 59351488HCID 59351488, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (30 mL) of ethyl 2-amino-5-methoxy-4-methylthiophene-3-carboxylate (1.0 g) in methylene chloride were added triphosgene (1.8 g) and triethylamine (3.0 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 1-phenylmethanamine (1.5 g), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (15 mL), sodium methoxide (1.0 g) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was neutralized with hydrochloric acid (10% methanol solution), insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (1.2 g, 84%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in methanol (15 mL)
  6. additionsodium methoxide (1.0 g) was added
  7. stirringthe mixture was stirred at 60° C. for 2 hr
  8. filtrationwas filtered off
  9. customthe solvent was evaporated under reduced pressure
  10. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-41b5c5b3d2fa49c2b3d678e1363b59e7
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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