3-Bromo-1,1,1-trifluoro-2-propanone → 2-Thiazolamine, 4-(trifluoromethyl)-

HRID 1660756Notes

Reaction equation

HRID 1660756 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH2:6][C:7](=O)[C:8]([F:11])([F:10])[F:9]>C(O)C>[F:9][C:8]([F:11])([F:10])[C:7]1[N:1]=[C:2]([NH2:4])[S:3][CH:6]=1

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 2723790Thiourea

Product 1

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-Yield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Add thiourea (4.0 g, 52.3 mmol) and 3-bromo-1,1,1-trifluoropropan-2-one (5.5 mL, 10 g, 52.3 mmol) to ethanol (100 mL) and heat at 50° C. for 2 h. Cool to room temperature and concentrate to dryness. Dissolve the residue in water and adjust the pH to >12 with 2 M NaOH. Extract with diethyl ether (4×). Dry the combined organic extracts with sodium sulfate, filter, and concentrate under vacuum. Purify the resulting material by silica gel chromatography (CH2Cl2) to obtain the title compound (6.9 g, 79%). ES/MS m/z 169 (M+1)+.

Workup

  1. temperatureCool to room temperature
  2. concentrationconcentrate to dryness
  3. dissolutionDissolve the residue in water
  4. extractionExtract with diethyl ether (4×)
  5. dry with materialDry the combined organic extracts with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the resulting material by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-c3e34903a96a427884953ca985902bf5
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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