Benzyl isocyanate → N-(6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(phenylmethyl)urea

HRID 129181Notes

Reaction equation

HRID 129181 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([NH:14][C:15]([NH:17]C3C=CC=CC=3)=[O:16])[C:7]=2[CH:24]=1)#[N:2].[CH2:25](N=C=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[CH2:9][CH:8]([NH:14][C:15]([NH:17][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:16])[C:7]=2[CH:24]=1)#[N:2]

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 9973362N-(6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-phenylurea

Product 1

HCID 15295557N-(6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(phenylmethyl)ureaYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the title D compound from Example 8 (0.50 g, 2.47 mmoles) and benzyl isocyanate (0.33 g, 2.47 mmoles) in anhydrous ethanol (4 ml) was heated at reflux for 3 hours and cooled to room temperature. The reaction product precipitated from solution. It was collected by suction filtration; the solid was triturated with diisopropyl ether and dried under vacuum to obtain 0.71 g of the title compound as a white solid, m.p. 168°-169° C. 1H NMR (DMSO-d6) δ7.59 (s, 1H), 7.56 (s, 1H), 7.38-7.24 (m, 5H) 6.89 (d, J=8.21 Hz, 1H), 6.56 (t, J=5.87 Hz, 1H), 6.50 (d, J=8.21 Hz, 1H), 4.94 (M, 1H), 4.30 (d, J=5.86 Hz, 2H), 2.10 (m, 1H), 1.74 (m, 1H), 1.41 (s, 3H), 1.28 (s, 3H). 13C NMR (DMSO-d6) δ158.11, 157.19, 140.78, 132.25, 132.08, 128.22, 126.93, 126.61, 126.12, 119.18, 118.03, 102.02, 77.28, 43.01, 41.95, 38.81, 29.08, 24.42.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe reaction product precipitated from solution
  3. filtrationIt was collected by suction filtration
  4. customthe solid was triturated with diisopropyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5c21c1c686fa42908053922f40b53a30
Source dataset
uspto-grants-1995_11
Patent number
US05466817

Reaction notes

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