Thioacetamide → HCID 58257109, compound

HRID 2093788Notes

Reaction equation

HRID 2093788 reaction equation
BrCC(C1C=C(C)C([N+]([O-])=O)=CC=1C)=O.C(=S)(N)C.[CH3:20][C:21]1[CH:26]=[C:25]([N+:27]([O-])=O)[C:24]([CH3:30])=[CH:23][C:22]=1[C:31]1[N:32]=[C:33]([CH3:36])[S:34][CH:35]=1>C(O)C.CO.[Pd]>[CH3:30][C:24]1[CH:23]=[C:22]([C:31]2[N:32]=[C:33]([CH3:36])[S:34][CH:35]=2)[C:21]([CH3:20])=[CH:26][C:25]=1[NH2:27]

Participants

7

Reactant 3

HCID 2723949ThioacetamideHCID 67167949HCID 67167949, compoundHCID 86653321HCID 86653321, compound

Product 1

HCID 58257109HCID 58257109, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromo-1-(2,5-dimethyl-4-nitrophenyl)ethanone (70 mg, 0.26 mmol) and ethanethioamide (30 mg, 0.4 mmol) in ethanol (2 mL) was heated in a microwave at 150° C. for 20 min. The obtained 4-(2,5-dimethyl-4-nitrophenyl)-2-methylthiazole was dissolved in methanol (10 mL). To the solution was added Pd/C (10%). The reaction mixture was degassed and purged with H2 for several times and stirred under 1 atm. hydrogen gas overnight. The mixture was filtered and concentrated to afford 2,5-dimethyl-4-(2-methylthiazol-4-yl)aniline. ESMS m/z 219 (M+H+).

Workup

  1. customThe reaction mixture was degassed
  2. custompurged with H2 for several times
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dee6aa4163ce410bbade37f993ff9ef5
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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