NaNCO → N-(2,3-Dihydro-1-benzofuran-6-yl)-N-propan-2-ylurea

HRID 1658286Notes

Reaction equation

HRID 1658286 reaction equation
[CH:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]2[CH2:9][CH2:10][O:11][C:7]=2[CH:6]=1)([CH3:3])[CH3:2].[N-:14]=[C:15]=[O:16].[Na+]>C(O)(=O)C>[CH:1]([N:4]([C:5]1[CH:13]=[CH:12][C:8]2[CH2:9][CH2:10][O:11][C:7]=2[CH:6]=1)[C:15]([NH2:14])=[O:16])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11051568NaNCOHCID 21528943N-isopropyl-2,3-dihydro-6-benzofuranamine

Product 1

HCID 21528985N-(2,3-Dihydro-1-benzofuran-6-yl)-N-propan-2-ylurea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 12.2 g. of N-isopropyl-2,3-dihydro-6-benzofuranamine in 250 ml. of glacial acetic acid, cooled to 15°±5°C. is added 24.0 g. of sodium isocyanate. The mixture is stirred at room temperature for 18 hours and then concentrated in vacuo. The residue is treated with 200 ml. of 2N sodium hydroxide solution and then extracted twice with chloroform. The combined chloroform extracts are dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo to obtain an oil of 1-isopropyl-1-(2,3-dihydro-6-benzofuranyl)urea.

Workup

  1. additionis added 24.0 g
  2. concentrationconcentrated in vacuo
  3. additionThe residue is treated with 200 ml
  4. extractionof 2N sodium hydroxide solution and then extracted twice with chloroform
  5. dry with materialThe combined chloroform extracts are dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab6c2243ae02484d8993689a55aef0ee
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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