Benzylamine → HCID 58234965, compound

HRID 1919355Notes

Reaction equation

HRID 1919355 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1OS(C1C=CC(C)=CC=1)(=O)=O)=[O:5])[CH3:2].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[NH:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 58234936HCID 58234936, compound

Product 1

HCID 58234965HCID 58234965, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-methyl-4-(toluene-4-sulfonyloxy)-thiazole-5-carboxylic acid ethyl ester (2.0 g, 5.865 mmol) in 1,4-dioxane (50 mL) was added benzylamine (1.92 mL, 17.6 mmol) and the mixture was heated at 120° C. for 6 h. The reaction mixture was cooled to RT and partitioned between EtOAc and an aqueous solution of HCl (1 M). The organic layer was isolated, washed with brine, then dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a yellow solid (0.80 g, 49%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. custompartitioned between EtOAc
  3. customThe organic layer was isolated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-4297aaf141a3455b839424cf119062eb
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

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