Methane → HCID 178441331, compound

HRID 556710Notes

Reaction equation

HRID 556710 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:23])[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[F:22])/[N:7]([CH2:24][CH2:25][OH:26])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C.C(=O)(OC(Cl)(Cl)Cl)[O:36][C:37](Cl)(Cl)[Cl:38]>CCOCC>[C:37]([Cl:38])(=[O:36])[O:26][CH2:25][CH2:24][N:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[S:9]/[C:8]/1=[N:10]\[C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:15]=[CH:14][C:13]=1[F:22]

Participants

6

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 94429TriphosgeneHCID 178441330HCID 178441330, compound

Product 1

HCID 178441331HCID 178441331, compoundYield 195.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of Example 61A (300 mg, 0.768 mmol) and triethylamine (233 mg, 2.305 mmol) in Et2O (5 mL) was added activated charcoal (10 mg, 0.768 mmol), followed by addition of bis(trichloromethyl) carbonate (114 mg, 0.384 mmol) and the mixture was stirred for 2 hr. The reaction was filtered, and concentrated to give the title compound as an oil (340 mg, 0.751 mmol, 98%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33 (s, 9H) 3.80 (t, J=5.43 Hz, 2H) 4.27 (t, J=5.43 Hz, 2H) 7.32 (s, 1H) 7.46-7.56 (m, 1H) 7.88-7.97 (m, 1H) 8.24-8.33 (m, 1H); MS (DCI) m/z 453 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-caaa15e452304a80adf43e0f0374b093
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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