Sodium dicyanamide → HCID 178512361, compound

HRID 1930744Notes

Reaction equation

HRID 1930744 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([CH2:21][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[NH:19][CH:20]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[N-:29]([C:32]#[N:33])[C:30]#[N:31].[Na+]>CN(C)C=O.Cl>[C:30]([N:29]=[C:32]([NH2:33])[NH:4][C:3]1[CH:5]=[CH:6][C:7]([O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[N:17]=[C:18]([CH2:21][O:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:19][CH:20]=3)=[CH:14][CH:15]=2)=[CH:8][C:2]=1[F:1])#[N:31]

Participants

5

Reactant 2

HCID 4350929Sodium dicyanamideHCID 178507749HCID 178507749, compound

Product 1

HCID 178512361HCID 178512361, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

In a sealed glass tube suitable for microwave heating, the compound 2-fluoro-4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}aniline (0.1 g, 0.27 mmol) and sodium dicyanamide (37 mg, 0.4 mmol) in 2.5 ml of dimethylformamide and 0.5 ml of hydrochloric acid 1N are heated at 75° C. in a microwave oven (Biotage, Emrys Optimiser) for 900 seconds. The reaction medium is evaporated to dryness. After passing the residue obtained through a silica column (eluent dichloromethane/ethanol 93/7), a solid in the form of white powder is obtained with a yield of 31%.

Workup

  1. temperatureIn a sealed glass tube suitable for microwave heating
  2. customThe reaction medium is evaporated to dryness
  3. customobtained through a silica column (eluent dichloromethane/ethanol 93/7)
  4. customa solid in the form of white powder is obtained with a yield of 31%

Sources & evidence

ORD record
ord-3a254c6bcd24433f9686f003631cae1c
Source dataset
uspto-grants-2012_05
Patent number
US08188133B2

Reaction notes

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