Cyanamide → HCID 178512258, compound

HRID 1532762Notes

Reaction equation

HRID 1532762 reaction equation
[N:1]#[C:2][NH2:3].C([O:7][C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][C:9]=1[N:16]=[C:17]=[N:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Br:25])C=C>C(#N)C>[OH:7][C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][C:9]=1[NH:16][C:17]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Br:25])=[N:3][C:2]#[N:1]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 15549378HCID 15549378, compound

Product 1

HCID 178512258HCID 178512258, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred mixture of cyanamide (560 mg, 13.33 mmol) and Huinig's base (2.6 ml) in acetonitrile was added a solution of N-(2-Allyloxy-4-cyanophenyl)-N′-(2-bromophenyl)-carbodiimide (600 mg, 1.69 mmol) in acetonitrile (30 ml) dropwise. The reaction was stirred at rt for 15 min, then the solvent was removed under reduced pressure and the residue hydrolyzed with 0.5 M sodium dihydrogen phosphate. Ethyl acetate extractions of the aqueous mixture were washed with 0.5 M sodium dihydrogen phosphate and brine. After drying (MgSO4) filtration and evaporation under reduced pressure afforded a crude tan solid (500 mg). This was chromatographed on silica gel (50/50 ethyl acetate/hexane) to give the title compound (455 mg, 95%). MS(ES−) m/e 394, 396 [M−H]−

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionEthyl acetate extractions of the aqueous mixture
  3. washwere washed with 0.5 M sodium dihydrogen phosphate and brine
  4. customAfter drying
  5. filtration(MgSO4) filtration and evaporation under reduced pressure
  6. customafforded a crude tan solid (500 mg)
  7. customThis was chromatographed on silica gel (50/50 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1b0f48dde62d4bdba0d0558574c61b1a
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

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