3-Chloro-2-butanone → 3-(4,5-Dimethyl-2-thiazolyl)benzenamine

HRID 1690672Notes

Reaction equation

HRID 1690672 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[S:6].Cl[CH:12]([CH3:16])[C:13](=O)[CH3:14]>CCO.CCOC(C)=O>[CH3:16][C:12]1[N:7]=[C:5]([C:4]2[CH:3]=[C:2]([NH2:1])[CH:10]=[CH:9][CH:8]=2)[S:6][C:13]=1[CH3:14]

Participants

5

Reactant 2

HCID 200263-Chloro-2-butanoneHCID 20608973-Aminobenzenecarbothioamide

Product 1

HCID 71485673-(4,5-Dimethyl-2-thiazolyl)benzenamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-amino-thiobenzamide (200 mg, 1.31 mmol, 1 eq.) in EtOH (4 mL) is added 3-chloro-2-butanone (140 mg, 1.31 mmol, 1 eq.). The mixture is heated at 100° C. for 72 h. After cooling to room temperature, the reaction is diluted with EtOAc and sequentially washed with saturated aqueous NaHCO3, H2O and saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (2:1 hexanes/EtOAc) to give 3-(4,5-Dimethyl-thiazol-2-yl)-phenylamine as a yellow oil. [MS: (ES+) 205.1 (M+1)+].

Workup

  1. temperatureAfter cooling to room temperature
  2. washsequentially washed with saturated aqueous NaHCO3, H2O and saturated aqueous NaCl
  3. dry with materialThe organic solution is dried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue is purified by silica gel chromatography (2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-530651dbaa1b4d779602aa328a493827
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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