Methane → HCID 178441331, compound

HRID 2196825Notes

Reaction equation

HRID 2196825 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, 2 H) 4.27 (t, J=5.43 Hz, 2 H) 7.32 (s, 1 H) 7.46-7.56 (m, 1 H) 7.88-7.97 (m, 1 H) 8.24-8.33 (m, 1 H); MS (DCI) m/z 453 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6d23f5b7f656439386ab5638b522380c
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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