Benzyl isocyanate → 4-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide

HRID 583775Notes

Reaction equation

HRID 583775 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([CH3:20])=[C:17]([NH2:19])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH2:21]([N:28]=[C:29]=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([CH3:20])=[C:17]([NH:19][C:29]([NH:28][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:30])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 611175195-Methyl-4-amino-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide

Product 1

HCID 101271134-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amideYield 37.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-methyl-4-amino-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide from Step 2 (0.6 g, 2.1 mmol) and benzyl isocyanate (0.28 g, 2.1 mmol) in 1,4-dioxane (100 mL) was stirred under an inert atmosphere and heated to reflux. After 30 minutes, the mixture was allowed to cool, and the solvent was removed under reduced pressure. The residue was triturated in a small amount of acetonitrile, cooled, and filtered to afford 0.33 g of 4-(3-benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide. A sample was recrystallized from methanol to give product with a mp 194-195° C.

Workup

  1. temperatureheated to reflux
  2. temperatureto cool
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was triturated in a small amount of acetonitrile
  5. temperaturecooled
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b6767c996fff46b09cdeac2da97f0e15
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

Loading…