NaNCO → N-(2,3-Dihydro-1-benzofuran-4-yl)-N-propan-2-ylurea

HRID 1658280Notes

Reaction equation

HRID 1658280 reaction equation
[CH:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[O:13][CH2:12][CH2:11][C:10]=12)([CH3:3])[CH3:2].[N-:14]=[C:15]=[O:16].[Na+]>C(O)(=O)C>[CH:1]([N:4]([C:5]1[C:10]2[CH2:11][CH2:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)[C:15]([NH2:14])=[O:16])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11051568NaNCOHCID 21529025N-isopropyl-2,3-dihydro-4-benzofuranamine

Product 1

HCID 21529030N-(2,3-Dihydro-1-benzofuran-4-yl)-N-propan-2-ylurea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7.4 g. of N-isopropyl-2,3-dihydro-4-benzofuranamine in 200 ml. of glacial acetic acid, cooled to 15°± 5°C. is added 2.5 g. of sodium isocyanate. The mixture is stirred at room temperature for 15 hours and then concentrated in vacuo. The residue is treated with 150 ml. of 2N sodium hydroxide and then extracted with chloroform. The chloroform extract is dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo to give an oil of 1-isopropyl-1-(2,3-dihydro-4-benzofuranyl) urea.

Workup

  1. additionis added 2.5 g
  2. concentrationconcentrated in vacuo
  3. additionThe residue is treated with 150 ml
  4. extractionof 2N sodium hydroxide and then extracted with chloroform
  5. extractionThe chloroform extract
  6. dry with materialis dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d2471aef00f46b1a2af337e7c2e25f5
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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