Sodium Bicarbonate → 4-Cyclobutyl-1,3-thiazol-2-amine

HRID 1828445Notes

Reaction equation

HRID 1828445 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH2:6][C:7]([CH:9]1[CH2:12][CH2:11][CH2:10]1)=O.C(=O)([O-])O.[Na+]>C(O)C>[CH:9]1([C:7]2[N:1]=[C:2]([NH2:4])[S:3][CH:6]=2)[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 110629402-Bromo-1-cyclobutylethan-1-one

Product 1

HCID 220636344-Cyclobutyl-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Thiourea (2.3 g, 30.0 mmol) was dissolved in ethanol (100 ml), added with 2-bromo-1-cyclobutyl-1-ethanone synthesized in the same manner as in Example 1, (E), and then heated to 100° C. The reaction solution was stirred for 1 hour, then returned to room temperature, neutralized with saturated sodium hydrogencarbonate and extracted with chloroform. The collected organic layer was washed with saturated brine, dried over magnesium sulfate and then concentrated under reduced pressure. The title compound was obtained as the residue without purification as a brown oily substance (5.4 g, 100%).

Workup

  1. customsynthesized in the same manner as in Example 1, (E),
  2. customreturned to room temperature
  3. extractionextracted with chloroform
  4. washThe collected organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8187ae78d1c4a36845fb1374412f289
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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