Trichloroacetyl isocyanate → HCID 22050095, compound

HRID 1832115Notes

Reaction equation

HRID 1832115 reaction equation
[Br:1][C:2]1[C:3](=[O:28])[N:4]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].ClC(Cl)(Cl)[C:31]([N:33]=C=O)=[O:32]>ClCCl.O1CCCC1>[C:31](=[O:32])([O:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:4]2[C:5]([CH3:18])=[CH:6][C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:2]([Br:1])[C:3]2=[O:28])=[CH:21][CH:22]=1)[NH2:33]

Participants

5

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 22051009HCID 22051009, compound

Product 1

HCID 22050095HCID 22050095, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound of Example 206 (0.868 g, 1.93 mmol) was suspended in dichloromethane (7.0 mL). Trichloroacetyl isocyanate (4.00 mL, 0.53 M in toluene, 2.12 mmol) was added. The resulting mixture was stirred at room temperature for 3 hours then diluted with tetrahydrofuran (50 mL) and Al2O3 (5.0 g) was added and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through a pad of Celite® washing with methonal. The filtrate was then concentrated and the residue was redissolved in tetrahydrofuran (30 mL). Al2O3 (5.0 g) was added and the mixture was heated to 40° C. for 3 hours. After cooling to room temperature, the reaction was filtered through a pad of Celite ® washing with methanol. The filtrate was concentrated and the resulting solid was washed with diethyl ether to give an off-white solid (0.831 g, 87%). 1H NMR (400 MHz, CDCl3) δ 7.54 (app q, J=7.7 Hz, 1H), 7.25 (d, J=8.2 Hz, 2H), 7.13 (d, J=8.2 Hz, 2H), 6.25 (app dt, J=2.0, 8.3 Hz, 1H), 6.86-6.30 (m, 1H), 5.97 (s, 1H), 5.32 (s, 2H), 5.18 (s, 2H), 5.02 (s, 2H), 4.81 (br s, 2H), 2.25 (s, 3H). ES-HRMS m/z 493.0580 (M+H calcd for C22H20BrF2N2O4 requires 493.0569).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature overnight
  3. filtrationThe reaction mixture was filtered through a pad of Celite®
  4. washwashing with methonal
  5. concentrationThe filtrate was then concentrated
  6. dissolutionthe residue was redissolved in tetrahydrofuran (30 mL)
  7. additionAl2O3 (5.0 g) was added
  8. temperaturethe mixture was heated to 40° C. for 3 hours
  9. temperatureAfter cooling to room temperature
  10. filtrationthe reaction was filtered through a pad of Celite ®
  11. washwashing with methanol
  12. concentrationThe filtrate was concentrated
  13. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-6b118660b61847549f34663bf1d7122e
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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