Trichloroacetyl isocyanate → HCID 24821336, compound

HRID 1028465Notes

Reaction equation

HRID 1028465 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].ClC(Cl)(Cl)[C:28]([N:30]=C=O)=[O:29]>C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([NH:23][C:28]([NH2:30])=[O:29])[CH3:22])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 69443896HCID 69443896, compound

Product 1

HCID 24821336HCID 24821336, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1F (0.15 g, 0.0004 mol) in methylene chloride (5 mL) was added trichloroacetyl isocyanate (0.08 mL, 0.0006 mol) and the mixture was stirred at room temperature for 15 minutes, and concentrated. The residue was dissolved in methanol (10 mL) and refluxed with a few drops of saturated sodium carbonate solution for 0.5 hours. The mixture was cooled to room temperature, concentrated to dryness and triturated with methanol (15 mL) and water (2 mL) to give 0.15 g of the title compound (88% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.23-1.34 (m, 9 H) 4.55-4.75 (m, 2 H) 5.42 (s, 2 H) 6.44 (d, J=8.09 Hz, 1 H) 6.97-7.05 (m, 2 H) 7.25-7.36 (m, 4 H) 7.49 (d, J=8.09 Hz, 2 H) 7.65 (s, 1 H). MS (ESI), m/z 397.9 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol (10 mL)
  3. temperaturerefluxed with a few drops of saturated sodium carbonate solution for 0.5 hours
  4. temperatureThe mixture was cooled to room temperature
  5. concentrationconcentrated to dryness
  6. customtriturated with methanol (15 mL) and water (2 mL)

Sources & evidence

ORD record
ord-4839932c576b40a5b0da6a5f60d45e12
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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