Benzenesulfonyl chloride → HCID 12050647, compound

HRID 369998Notes

Reaction equation

HRID 369998 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][NH:12][CH2:13][C:14]([CH3:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18].C(N(CC)C(C)C)(C)C>C1COCC1.C(OCC)(=O)C>[CH3:11][N:12]([CH2:13][C:14]([CH3:26])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 12050646HCID 12050646, compound

Product 1

HCID 12050647HCID 12050647, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzenesulfonyl chloride (0.280 mL, 388 mg, 2.19 mmol) was added dropwise over 5 min to a solution of N-methyl-(2,5-dimethyl-2-phenylhex-4-en-1-yl)amine (415 mg, 1.91 mmol) and N,N-diisopropylethylamine (0.520 mL, 386 mg, 2.99 mmol) in THF (5.0 mL) at RT. After 16 h, the reaction mixture was diluted with 30 mL of ethyl acetate and washed with 15 mL each of 2 N aqueous HCl, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was dried over sodium sulfate and evaporated. The crude product was purified by flash column chromatography on silica gel, eluting with 4% ethyl acetate in hexane, to give 0.59 g of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.72 (d, 2H, J=7.5 Hz), 7.55 (t, 1H, J=7.5 Hz), 7.48 (t, 2H, J=7.5 Hz), 7.33-7.23 (m, 4H), 7.17 (t, 1H, J=7 Hz), 4.83 (bt, 1H, J=7 Hz), 3.40 (d, 1H, J=13 Hz), 2.94 (d, 1H, J=13 Hz), 2.50 (dd, 1H, J=15, 6 Hz), 2.33 (dd, 1H, J=15, 8 Hz), 2.09 (s, 3H), 1.59 (s, 6H), 1.42 (s, 3H). Mass spectrum (NH3 /CI): m/z=358 (M+1).

Workup

  1. washwashed with 15 mL each of 2 N aqueous HCl, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by flash column chromatography on silica gel
  5. washeluting with 4% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d660765bb7374b2c99cd8b5e6d300348
Source dataset
uspto-grants-2000_10
Patent number
US06140349

Reaction notes

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