Sodium Cyanate → HCID 59259041, compound

HRID 641838Notes

Reaction equation

HRID 641838 reaction equation
[CH2:1]([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]2[CH2:29][CH2:28]2)=[CH:23][CH:22]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:30][C:31]#[N:32].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[CH2:1]([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]3[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)=[N:32][C:31]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 517096Sodium CyanateHCID 59259056HCID 59259056, compound

Product 1

HCID 59259041HCID 59259041, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 460 mg (1.21 mmol) of (2-benzylamino-5-propargyloxyphenyl)-(4-cyclopropyl-phenyl)-methanone (step E) and 118 mg (1.81 mmol) sodium cyanate in 20 ml glacial acetic acid is stirred at rt for 8 h. Then the mixture is diluted with water and ethyl acetate. The layers are separated and the organic phase is washed with water and bicarbonate solution. Chromatography (dichloromethane/MeOH) of the crude product affords a yellow foam. m.p. 112-113° C.

Workup

  1. customThe layers are separated
  2. washthe organic phase is washed with water and bicarbonate solution

Sources & evidence

ORD record
ord-8c247259816945899e2dfd2b0fd4d4b8
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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