1-Fluoro-4-(1-isothiocyanatoethyl)benzene → HCID 10094291, compound

HRID 1352515Notes

Reaction equation

HRID 1352515 reaction equation
[CH2:1]([C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]1[CH:31]=[CH:30][C:24]([CH:25]([N:27]=[C:28]=[S:29])[CH3:26])=[CH:23][CH:22]=1>CN(C)C=O>[CH2:1]([C:8]1[C:9]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:28]([NH:27][CH:25]([C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:31][CH:30]=3)[CH3:26])=[S:29])=[CH:17][CH:18]=2)=[N:10][O:11][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5195361-Fluoro-4-(1-isothiocyanatoethyl)benzeneHCID 21100737HCID 21100737, compound

Product 1

HCID 10094291HCID 10094291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-benzyl-isoxazol-3-yl)-phenylamine and 4-fluoro-α-methyl-benzyl isothiocyanate in dimethylformamide (5 mL) is stirred for 12 hours at room temperature. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.4 g crude product as a yellow solid. The latter is recrystallized from ethyl acetate/hexane to give 0.9 g product as a yellow solid. MS: m/z 433 (M+H)+.

Workup

  1. customThe reaction mixture is then partitioned between ethyl acetate and water
  2. washThe organic layer is washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give 1.4 g crude product as a yellow solid
  6. customThe latter is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1776ada67fe54e45ae9af346f1806bc4
Source dataset
uspto-grants-2007_05
Patent number
US07220768B2

Reaction notes

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