Triethylamine → HCID 67247411, compound

HRID 2425109Notes

Reaction equation

HRID 2425109 reaction equation
C(N(CC)CC)C.Br[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[N+:17]([O-:19])=[O:18].[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([Br:30])=[C:25]([SH:31])[CH:24]=1>ClCCl.O>[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([Br:30])=[C:25]([S:31][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[N+:17]([O-:19])=[O:18])[CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 122325513-chloro-2-nitrobenzyl bromideHCID 67246834HCID 67246834, compound

Product 1

HCID 67247411HCID 67247411, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.16 mL, 8.61 mmol) was added to a stirred solution of compound of Example 37a (2.87 g, 11.78 mmol) and compound of Example 1f (1.5 g, 5.74 mmol) in dry dichloromethane (75 mL). The reaction mixture was stirred at 0° C. for 20 min, was poured in water (100 mL) and extracted with chloroform (2×50 mL). The combined extract was washed with water (50 mL), brine (50 mL) and concentrated under vacuum to obtain the crude product, which was purified by column chromatography (silica gel, 5% ethyl acetate in pet ether 60-80° C.) to obtain the title compound. Yield: 1.93 g, (77.82%); 1H NMR (DMSO-d6, 300 MHz): δ 2.55 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 4.25 (s, 2H, CH2), 7.45 (s, 1H, Ar), 7.50-7.60 (m, 2H, Ar), 7.75 (s, 1H, Ar), 7.85 (s, 1H, Ar); MS: m/e (ES−) 431 (M−1).

Workup

  1. extractionextracted with chloroform (2×50 mL)
  2. extractionThe combined extract
  3. washwas washed with water (50 mL), brine (50 mL)
  4. concentrationconcentrated under vacuum
  5. customto obtain the crude product, which
  6. customwas purified by column chromatography (silica gel, 5% ethyl acetate in pet ether 60-80° C.)

Sources & evidence

ORD record
ord-4ecc9adc9b3f486093e6dc713fa77f2c
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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