Hydrochloric Acid → 1-(4-(Oxazol-5-yl)phenyl)guanidine

HRID 1930536Notes

Reaction equation

HRID 1930536 reaction equation
Cl.[O:2]1[C:6]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:5][N:4]=[CH:3]1.[NH:14]=[C:15]=[NH:16].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[O:2]1[C:6]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:15]([NH2:16])=[NH:14])=[CH:9][CH:8]=2)=[CH:5][N:4]=[CH:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 160435CarbodiimideHCID 5177474-(1,3-Oxazol-5-yl)aniline

Product 1

HCID 1785124711-(4-(Oxazol-5-yl)phenyl)guanidineYield 110.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydrochloric acid (4.04 mL, 24.35 mmol) was added to a solution of 4-(oxazol-5-yl)aniline (5 g, 31.22 mmol) and carbodiimide (1.444 g, 34.34 mmol) in ethanol (50 mL). The resulting mixture was heated to reflux for 5 h. The reaction mixture was concentrated under reduced pressure and potassium carbonate (2.59 g, 18.73 mmol) in water (50.00 mL) was added. The formed crystals were filtered off, washed with several portions of potassium carbonate (aq) and dried over night under reduced pressure. The crude solid was slurried in DCM and filtered to give 1-(4-(oxazol-5-yl)phenyl)guanidine (7.00 g, 86%). No further purification. MS (ESI+)/(ESI−) m/z 203/201

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 5 h
  3. additionwas added
  4. filtrationThe formed crystals were filtered off
  5. washwashed with several portions of potassium carbonate (aq)
  6. customdried over night under reduced pressure
  7. filtrationfiltered

Sources & evidence

ORD record
ord-41d765b166734088b566c550347a5351
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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