3-Bromo-1,1,1-trifluoro-2-propanone → HCID 67028825, compound

HRID 2061869Notes

Reaction equation

HRID 2061869 reaction equation
[Br:1][C:2]1[C:3]([C:16](=[S:18])[NH2:17])=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+].[F:24][C:25]([F:31])([F:30])[C:26]([CH2:28]Br)=[O:27]>O1CCCC1>[Br:1][C:2]1[C:3]([C:16]2[S:18][CH2:28][C:26]([OH:27])([C:25]([F:31])([F:30])[F:24])[N:17]=2)=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 86643630HCID 86643630, compound2×

Product 1

HCID 67028825HCID 67028825, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 2 L round bottom flask was charged tert-butyl 5-bromo-4-carbamothioylpyridin-2-ylcarbamate (Intermediate 85, 50 g, 151 mmol) in tetrahydrofuran (800 mL), then solid sodium bicarbonate (25.4 g, 302 mmol) was added followed by 1,1,1-trifluoro-3-bromoacetone (31 mL, 290 mmol). The resulting mixture (yellow suspension) was allowed to stir at room temperature overnight. The white suspension was filtered and the solid was washed with water (2.2˜2.5 L). The white solid was dried under vacuum to give 56.8g of white powder (85%)

Workup

  1. filtrationThe white suspension was filtered
  2. washthe solid was washed with water (2.2˜2.5 L)
  3. customThe white solid was dried under vacuum

Sources & evidence

ORD record
ord-f9f5564c1c2f4f1c8f3a75a0d7e28db4
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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