Sodium Cyanate → HCID 59259047, compound

HRID 1046367Notes

Reaction equation

HRID 1046367 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([O:32][CH3:33])[C:30]=1[OH:31])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]#[CH:16])=[CH:9][C:8]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=1)=O.[O-:34][C:35]#[N:36].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([O:32][CH3:33])[C:30]=1[OH:31])[CH2:5][N:6]1[C:7]2[C:8](=[CH:9][C:10]([O:13][CH2:14][C:15]#[CH:16])=[CH:11][CH:12]=2)[C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[N:36][C:35]1=[O:34]

Participants

4

Reactant 2

HCID 517096Sodium CyanateHCID 59259162HCID 59259162, compound

Product 1

HCID 59259047HCID 59259047, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 43.1 mg (0.093 mmol) of [2-(3-Chloro-4-hydroxy-5-methoxy-benzyl-amino)-5-prop-2-ynyloxy-phenyl]-(4-isopropyl-phenyl)-methanone in 1 ml of acetic acid is added 12.1 mg (0.186 mmol) of sodium cyanate. After stirring for 12 h at r.t. the solvent is removed in vacuo and the residue partitioned between saturated NaHCO3 solution and ethyl acetate. The organic layer is separated and the aqueous phase extracted twice with ethyl acetate. The combined organic extracts are dried (Na2SO4) and evaporated in vacuo. Flash chromatography (SiO2, hexane/ethyl acetate) affords the title compound as an amorphous yellow solid.

Workup

  1. customis removed in vacuo
  2. customthe residue partitioned between saturated NaHCO3 solution and ethyl acetate
  3. customThe organic layer is separated
  4. extractionthe aqueous phase extracted twice with ethyl acetate
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-7576d92b643e4836b08fe71a442e4306
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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