Cyanamide → HCID 15676053, compound

HRID 2072719Notes

Reaction equation

HRID 2072719 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[C:9](=O)[CH2:10][OH:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N:20]#[C:21][NH2:22].[OH-].[Na+]>O1CCCC1.O>[NH2:22][C:21]1[O:11][CH:10]=[C:9]([CH:8]([C:6]2[CH:5]=[CH:4][C:3]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:2]([F:1])[CH:7]=2)[CH3:13])[N:20]=1

Participants

6

Reactant 3

HCID 9864Cyanamide2×HCID 14798Sodium HydroxideHCID 15676007HCID 15676007, compound

Product 1

HCID 15676053HCID 15676053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-(2-Fluoro-4-biphenylyl)-2-oxo-1-butanol (3.57 g, 13.8 mmol) in tetrahydrofuran (35 ml) was added cyanamide (3.65 g, 77.6 mmol) in water and 2N-sodium hydroxide to pH 10. After the addition, the mixture was stirred overnight, then cyanamide (3.65 g, 77.6 mmol) was added to the reaction mixture to pH 10, the mixture was stirred overnight. The reaction mixture was extracted with ether and the extracts were washed with water, dried over and evaporated under reduced pressure to a residue, which was chromatographed to afford 2-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)oxazole as crystalline material (1.05 g, 27% yield): mp 150.5-151.5° C.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred overnight
  3. extractionThe reaction mixture was extracted with ether
  4. washthe extracts were washed with water
  5. customdried over and
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-f0106b1bd6eb4412aa1f362f7dea695d
Source dataset
uspto-grants-1990_04
Patent number
US04914112

Reaction notes

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