Sodium Cyanate → 1-[2-(2-Hydroxy-ethoxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

HRID 641830Notes

Reaction equation

HRID 641830 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:33]=[CH:32][CH:31]=[CH:30][C:6]=1[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]#[CH:18])=[CH:11][C:10]=1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=1)=O.[O-:34][C:35]#[N:36].[Na+]>C(O)(=O)C>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:33]=[CH:32][CH:31]=[CH:30][C:6]=1[CH2:7][N:8]1[C:9]2[C:10](=[CH:11][C:12]([O:15][CH2:16][C:17]#[CH:18])=[CH:13][CH:14]=2)[C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[N:36][C:35]1=[O:34]

Participants

4

Reactant 2

HCID 517096Sodium CyanateHCID 10433518{2-[2-(2-Hydroxy-ethoxy)-benzylamino]-5-prop-2-ynyloxy-phenyl}-(4-isopropyl-phenyl)-methanone

Product 1

HCID 592590401-[2-(2-Hydroxy-ethoxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 85 mg (0.192 mmol) {2-[2-(2-Hydroxy-ethoxy)-benzylamino]-5-prop-2-ynyloxy-phenyl}-(4-isopropyl-phenyl)-methanone in 2 ml acetic acid is added 25 mg (0.383 mmol) sodium cyanate. After stirring for 2 h the solvent is removed in vacuo and the residue is partitioned between CH2Cl2 and water. The organic layer is extracted with 2 M sodium hydroxide solution. After evaporation of the organic phase the product is obtained as a yellow oil.

Workup

  1. customis removed in vacuo
  2. customthe residue is partitioned between CH2Cl2 and water
  3. extractionThe organic layer is extracted with 2 M sodium hydroxide solution
  4. customAfter evaporation of the organic phase the product
  5. customis obtained as a yellow oil

Sources & evidence

ORD record
ord-cc7ed7d04a3d4f01b7d9cd801d564a76
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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