1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-yl)urea

HRID 2199619Notes

Reaction equation

HRID 2199619 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:11]=3[CH:10]=2)[O:3]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31]>O1CCCC1.C(OCC)(=O)C>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:18][C:16]2[CH:15]=[CH:14][C:12]3[S:13][C:9]([B:4]4[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:19])([CH3:1])[O:3]4)=[CH:10][C:11]=3[CH:17]=2)=[O:29])=[CH:23][C:22]=1[C:30]([F:31])([F:32])[F:33]

Participants

5

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 1254677282-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amine

Product 1

HCID 1317356921-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-yl)urea

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amine (825 mg, 3 mmol, 1 eq) in anhydrous tetrahydrofuran (15 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (678.3 mg, 1 eq) and the reaction solution was stirred at room temperature under nitrogen atmosphere overnight. The reaction was then diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted and concentrated under reduced pressure. 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-yl)urea was obtained as slightly brown colored foam in vacuo in the amount of 1.5 g which was used directly without further purification.

Workup

  1. washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe upper clear solution was decanted
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0a98bc16591492faa2543af9a7e9d5e
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

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