Pyridine → HCID 10689171, compound

HRID 431292Notes

Reaction equation

HRID 431292 reaction equation
N1C=CC=CC=1.[N+:7]([C:10]1[CH:30]=[CH:29][CH:28]=[CH:27][C:11]=1[CH2:12][O:13][C:14]([O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([CH2:21]O)=[CH:19][C:18]=1[CH3:26])=[O:15])([O-:9])=[O:8].[Cl:31]C(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[N+:7]([C:10]1[CH:30]=[CH:29][CH:28]=[CH:27][C:11]=1[CH2:12][O:13][C:14]([O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([CH2:21][Cl:31])=[CH:19][C:18]=1[CH3:26])=[O:15])([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 10782713HCID 10782713, compound

Product 1

HCID 10689171HCID 10689171, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (34 mL, 0.42 mmol) was added to a stirring mixture of 8h (56 mg, 0.17 mmol) and triphosgene (60 mg, 0.20 mmol) in a mixture of CDCl3 (1 mL) and CH2Cl2 (2.5 mL) at r.t. After 45 minutes, the reaction mixture was filtered through a pad of silica gel (5 g, 3 cm) washing with CH2Cl2 (20 mL) and concentrated in vacuo to yield pure 9h (53 mg, 90%) as a clear oil which became an off-white solid on addition of hexane: 1H NMR (270 MHz, CDCl3) d 2.20 (s, 6H), 4.50 (s, 2H), 5.70 (s, 2H), 7.09 (s, 2H), 7.50-7.56 (m, 1H), 7.69-7.72 (m, 2H), 8.16 (d, J=7.9 Hz, LH); 13C NMR (68 MHz, CDCl3) d 16.1, 64.7, 66.9, 125.4, 127.5, 128.8, 129.3, 130.3, 131.6, 134.1, 138.9, 147.3, 147.69, 152.7.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of silica gel (5 g, 3 cm)
  2. washwashing with CH2Cl2 (20 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56f3b6580e784f3f92d78237fa375348
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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