Water → 1-phenyl-N-(1,3-thiazol-2-ylmethyl)methanamine

HRID 651036Notes

Reaction equation

HRID 651036 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:9]1[CH:13]=[CH:12][N:11]=[C:10]1[CH:14]=O.O>C1(C)C=CC=CC=1>[CH2:1]([NH:8][CH2:14][C:10]1[S:9][CH:13]=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 47776191-phenyl-N-(1,3-thiazol-2-ylmethyl)methanamineYield 58.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of N-benzylamine (0.56 mL, 5.1 mmol) and 2-thiazolecarboxaldehyde (0.55 g, 4.9 mmol) in toluene was heated to reflux for 2 hours with azeotropic removal of water. The solution was cooled to room temperature and concentrated to an oil. This oil was dissolved in 15 mL of ethanol and treated with excess NaBH4 and the mixture stirred overnight. Acetone was added and the mixture stirred 30 minutes and concentrated to a soild mass. This mass was partitioned between 2N aqueous NaOH and 2 portions of ethyl ether. The combined ethereal extracts were washed with water, brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel to provide 0.59 g (57%) of the title compound.

Workup

  1. concentrationconcentrated to an oil
  2. dissolutionThis oil was dissolved in 15 mL of ethanol
  3. additiontreated with excess NaBH4
  4. additionAcetone was added
  5. stirringthe mixture stirred 30 minutes
  6. concentrationconcentrated to a soild mass
  7. customThis mass was partitioned between 2N aqueous NaOH and 2 portions of ethyl ether
  8. washThe combined ethereal extracts were washed with water, brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-74db08013dc7466199a32a173adbda77
Source dataset
uspto-grants-2001_08
Patent number
US06277871B1

Reaction notes

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