NaNCO → N-(2,3-Dihydro-1-benzofuran-5-yl)-N-propan-2-ylurea

HRID 1658283Notes

Reaction equation

HRID 1658283 reaction equation
[CH:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][CH2:11][CH2:10][C:9]=2[CH:13]=1)([CH3:3])[CH3:2].[N-:14]=[C:15]=[O:16].[Na+]>C(O)(=O)C>[CH:1]([N:4]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][CH2:11][CH2:10][C:9]=2[CH:13]=1)[C:15]([NH2:14])=[O:16])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11051568NaNCOHCID 21529005N-isopropyl-2,3-dihydro-5-benzofuranamine

Product 1

HCID 21529015N-(2,3-Dihydro-1-benzofuran-5-yl)-N-propan-2-ylurea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 14.2 g. of N-isopropyl-2,3-dihydro-5-benzofuranamine in 300 ml. of glacial acetic acid, cooled to 15°±5°C. is added 4.9 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 fulfate, filtered and concentrated in vacuo to obtain an oil of 1-isopropyl-1-(2,3-dihydro-5-benzofuranyl)urea.

Workup

  1. additionis added 4.9 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 fulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbe4d884e36d4e7abed926bfcffcb84c
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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