Trichloroacetyl isocyanate → HCID 22050095, compound

HRID 1867164Notes

Reaction equation

HRID 1867164 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 methanol. 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 methanol
  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-1ae7d63557af411eab1ceb68295fb2e9
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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