Triethylamine → HCID 21930326, compound

HRID 1243656Notes

Reaction equation

HRID 1243656 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31].C(N(CC)CC)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([CH:10]=1)[C:7]([NH:31][CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[O:27][CH3:26])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 812922-MethoxybenzylamineHCID 21930283HCID 21930283, compound

Product 1

HCID 21930326HCID 21930326, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-(4-trifluoromethoxy-benzenesulfonylamino)-benzoyl chloride (5.124 g, 11.6 mmol) was dissolved in tetrahydrofuran (100 mL) and the mixture was cooled in an ice bath below 5° C. 2-Methoxy-benzyl amine (1.8 mL, 13.8 mmol, 1.2 equivalents) and triethyl amine (1.9 mL, 13.6 mmol, 1.2 equivalents) were added to the mixture keeping the temperature below 10° C. The mixture was warmed to room temperature and the solvent was removed to dryness. The residue was partitioned between aqueous HCl (1M, 50 mL) and ethyl acetate (100 mL). The organic solvent was collected and concentrated to dryness. The resulting solid was dissolved in ethyl acetate and the solvent removed (2×25 mL). The resulting mixture was purified by column chromatography on silica with an eluent of 20% ethyl acetate in hexane. The solid was suspended in a mixture of 5% ethyl acetate in hexane (90 mL). The mixture was centrifuged and the solid dried at 40° C. overnight in vacuum oven. Recovery=4.85 g (75% yield). M/Z of [M−H]−=557, 1H NMR (CDCl3) δ=3.85 (s, 3H), 4.5 (sd, 2H), 6.5–6.6 (1H), 6.9–7.05 (4H), 7.3–7.4 (2H), 7.45 (1H), 7.5 (1H), 7.6 (1H), 7.8 (2H), 10.8 (br, 1H).

Workup

  1. temperaturethe mixture was cooled in an ice bath below 5° C
  2. customthe temperature below 10° C
  3. customthe solvent was removed to dryness
  4. customThe residue was partitioned between aqueous HCl (1M, 50 mL) and ethyl acetate (100 mL)
  5. customThe organic solvent was collected
  6. concentrationconcentrated to dryness
  7. dissolutionThe resulting solid was dissolved in ethyl acetate
  8. customthe solvent removed (2×25 mL)
  9. customThe resulting mixture was purified by column chromatography on silica with an eluent of 20% ethyl acetate in hexane
  10. additionThe solid was suspended in a mixture of 5% ethyl acetate in hexane (90 mL)
  11. customthe solid dried at 40° C. overnight in vacuum oven

Sources & evidence

ORD record
ord-7a22d57a152143deabb122775fc53e02
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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