3-Methyl-2-butanone → 4-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amine

HRID 2422270Notes

Reaction equation

HRID 2422270 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=O)[CH3:4].BrBr.[CH3:9][CH:10]([CH3:17])[CH2:11][CH2:12][NH:13][C:14]([NH2:16])=[S:15].C([O-])(=O)C.[Na+]>CO>[CH:2]([C:3]1[N:16]=[C:14]([NH:13][CH2:12][CH2:11][CH:10]([CH3:17])[CH3:9])[S:15][CH:4]=1)([CH3:6])[CH3:1]

Participants

6

Reactant 4

HCID 112513-Methyl-2-butanoneHCID 24408BromineHCID 517045Sodium AcetateHCID 2459097(3-Methyl-butyl)-thiourea

Product 1

HCID 230830994-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amineYield 21.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-methyl-2-butanone (2.64 g) in methanol (30 ml) was cooled to −30° C. bromine (4.8 g) was added, and heated to room temperature with stirring. To the obtained colorless solution were added N-(3-methylbutyl)thiourea (2.92 g) and sodium acetate (2.40 g) and the mixture was stirred with heating under reflux for 2 hrs. The reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The ethyl acetate layer was concentrated, and the residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 2:1 by volume ratio) to give the title compound (0.90 g, yield 21%) as a yellow oil.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred
  3. temperaturewith heating
  4. temperatureunder reflux for 2 hrs
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with ethyl acetate
  7. washwashed with water
  8. concentrationThe ethyl acetate layer was concentrated
  9. customthe residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 2:1 by volume ratio)

Sources & evidence

ORD record
ord-3e3b63acf6a647f381eb1d9d24bf8573
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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