1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 131735689, compound

HRID 2199613Notes

Reaction equation

HRID 2199613 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][C:7]([C:9]3[C:10]([NH2:17])=[N:11][CH:12]=[C:13]([N+:15]#[C-:16])[CH:14]=3)=[CH:8][C:4]=2[CH: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>[NH2:17][C:10]1[C:9]([C:7]2[S:6][C:5]3[CH:18]=[CH:19][C:2]([NH:1][C:28]([NH:27][C:24]4[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:30]([F:32])([F:31])[F:33])[CH:23]=4)=[O:29])=[CH:3][C:4]=3[CH:8]=2)=[CH:14][C:13]([N+:15]#[C-:16])=[CH:12][N:11]=1

Participants

5

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 125488006HCID 125488006, compound

Product 1

HCID 131735689HCID 131735689, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the stirring mixture of 3-(5-aminobenzo[b]thiophen-2-yl)-5-isocyanopyridin-2-amine (1.064 g, 4 mmol, 1 eq) in anhydrous tetrahydrofuran (25 mL) under nitrogen atmosphere was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (904 mg, 1 eq) and the reaction mixture was stirred at room temperature for three hours. 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 to lesser amount, to which was added a small amount of EtOAc-Hex (2:1). Upon a filtration, 1-(2-(2-amino-5-isocyanopyridin-3-yl)benzo[b]thiophen-5-yl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea was obtained as white solid in the amount of 1.37 g.

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 to lesser amount, to which
  5. additionwas added a small amount of EtOAc-Hex (2:1)
  6. filtrationUpon a filtration

Sources & evidence

ORD record
ord-14a817e3ae8545818cfbe3a1f83ca387
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

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