N-bromobutanimide → HCID 57513833, compound

HRID 2368420Notes

Reaction equation

HRID 2368420 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6].C1C(=O)N(Br)C(=O)C1.[NH2:25][C:26]([NH2:28])=[S:27]>O>[NH2:28][C:26]1[S:27][C:4]([C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[O:6])=[C:3]([C:2]([F:16])([F:15])[F:1])[N:25]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 2723790ThioureaHCID 27714764,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dione

Product 1

HCID 57513833HCID 57513833, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4,4,4-Trifluoro-1-(4-fluoro-phenyl)-butane-1,3-dione (15 g, 64 mmol) and NBS (11.4 g, 64.1 mmol) was ground together at RT, which incited to give a homogeneous mixture and then solidified to give crude brominated product. Water was added to rinse the solid. The solid was taken up in ethanol (50 mL), and thiourea (4.9 g, 64 mmol) was added. The mixture was heated at 85° C. for 4 h, cooled to RT and partitioned between ethyl acetate and aq. K2CO3. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 291.0 (MH+).

Workup

  1. customwas ground together at RT
  2. customto give a homogeneous mixture
  3. customto give crude brominated product
  4. washto rinse the solid
  5. temperaturecooled to RT
  6. custompartitioned between ethyl acetate and aq. K2CO3
  7. extractionThe organic extract
  8. dry with materialwas dried over MgSO4
  9. concentrationconcentrated
  10. customchromatographed

Sources & evidence

ORD record
ord-72628678439741fba4598f6d39b3d62b
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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