Water → HCID 29790482, compound

HRID 1643509Notes

Reaction equation

HRID 1643509 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[N:7]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[CH:9][CH:8]=1.O>C1(C)C=CC=CC=1>[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21552-AminothiazoleHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 29790482HCID 29790482, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-aminothiazole (3 g, 30 mmol) and 4-pyridinecarboxaldehyde (3.21 g, 30 mmol) in toluene (50 ml) was refluxed with a Dean-Stark water separator for 3 h. Solvent was removed under reduced pressure and the resulting yellow solid was dissolved in CH3OH (80 ml). The solution was carefully treated with sodium borohydride (1.8 g) and was stirred for 20 minutes. The reaction mixture was quenched with 1N NaOH and evaporated to dryness. The residue was dissolved in EtOAc, washed with brine and dried (MgSO4). Solvent was evaporated to give the crude intermediate N-(pyridin-4-ylmethyl)-1,3-thiazol-2-amine as a brown solid (4.2 g).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe resulting yellow solid was dissolved in CH3OH (80 ml)
  3. additionThe solution was carefully treated with sodium borohydride (1.8 g)
  4. customThe reaction mixture was quenched with 1N NaOH
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customSolvent was evaporated

Sources & evidence

ORD record
ord-b85555103e2043918391304f9d3189aa
Source dataset
uspto-grants-2012_02
Patent number
US08119819B2

Reaction notes

Loading…