Thiourea → HCID 16768804, compound

HRID 926845Notes

Reaction equation

HRID 926845 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17]>CO>[F:12][C:11]([F:14])([F:13])[C:7]1[CH:6]=[C:5]([C:3]2[S:17][C:16]([NH2:18])=[N:15][CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 16768804HCID 16768804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Into a 100-mL round bottom flask, was placed a solution of 2-bromo-1-(3-(trifluoromethyl)phenyl)ethanone (2.5 g, 9.40 mmol, 1.00 equiv) in methanol (50 mL), and thiourea (710 mg, 9.33 mmol, 1.00 equiv). The resulting solution was stirred overnight at 75° C. in an oil bath. The reaction mixture was cooled with a water/ice bath. The solids were collected by filtration. The residue was dissolved in 200 mL of ethyl acetate. The resulting mixture was washed with 1×50 mL of sodium hydroxide (1 N) and 2×50 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in 2.2 g (96%) of 5-(3-(trifluoromethyl)phenyl)thiazol-2-amine as a white solid.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. temperatureThe reaction mixture was cooled with a water/ice bath
  3. filtrationThe solids were collected by filtration
  4. dissolutionThe residue was dissolved in 200 mL of ethyl acetate
  5. washThe resulting mixture was washed with 1×50 mL of sodium hydroxide (1 N) and 2×50 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 2.2 g (96%) of 5-(3-(trifluoromethyl)phenyl)thiazol-2-amine as a white solid

Sources & evidence

ORD record
ord-c455b9125c324d5284e21a907a74497e
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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