HCID 15481243, compound → HCID 15481244, compound

HRID 1873133Notes

Reaction equation

HRID 1873133 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:19]3[C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[S:22][C:18]=3[C:17]([CH3:27])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]3)=[CH:5][C:4]=1[CH3:28].Cl.[NH+]1C=CC=CC=1>>[CH3:9][C:8]1[CH:7]=[C:6]([C:10]2[C:19]3[C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[S:22][C:18]=3[C:17]([CH3:27])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]3)[CH:5]=[C:4]([CH3:28])[C:3]=1[OH:2]

Participants

3

Reactant 2

HCID 15481243HCID 15481243, compoundHCID 21584435Pyridinium hydrochloride2×

Product 1

HCID 15481244HCID 15481244, compoundYield 64.1%

Conditions

Temperature
240 °C

Procedure

A mixture of 11-(4-methoxy-3,5-dimethyl-phenyl)-6-methyl-benzo[b]naphtho[2,3-d]thiophene (0.55 g, 1.44 mmol) and pyridinium hydrochloride (1.0 g, 8.64 mmol) was heated in a 240° C. oil bath for 1.25 hour. During this time an additional amount of pyridinium hydrochloride was added (1.0 g, 8.64 mmol). The reaction mixture was cooled to room temperature and partitioned between dilute HCl and ether. Silica gel was added to the ether phase and the solvent was removed. The adsorbate was flash chromatographed (9:1 petroleum ether:ethyl acetate) to provide a light yellow solid (340 mg). This solid was recrystallized from acetic acid to provide the title compound as a light yellow solid (0.215 g, 41%): mp 147-149° C.: NMR (CDCl3); δ 8.15 (ddd, J=8, 1, 1 Hz, 1H), 7.80 (ddd, J=8, 1, 1 Hz, 1H), 7.71 (ddd, J=8, 1, 1 Hz, 1H), 7.56 (ddd, J=8, 7, 1 Hz, 1H), 7.39 (ddd, J=8, 7, 1 Hz, 1H), 7.35 (ddd, J=8, 8, 1 Hz, 1H), 7.09 (ddd, J=8, 7, 1 Hz, 1H), 7.01 (s, 2H), 6.79 (ddd, J=8, 1, 1 Hz, 1H), 2.96 (s, 3H), 2.36 (s, 6H); MS (EI): 368 (100%, MI); Anal. Calc. for C25H20OS: C, 81.49, H, 5.47, N, 0.00. Found: C, 81.62, H, 5.32, N, -0.03.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between dilute HCl and ether
  3. additionSilica gel was added to the ether phase
  4. customthe solvent was removed
  5. customchromatographed (9:1 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-44d2adc00c8145ffa2d46ad61158b43a
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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