Triethylamine → HCID 14479946, compound

HRID 973971Notes

Reaction equation

HRID 973971 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].Cl.[NH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].C(N(CC)CC)C.[CH3:24][C:25]([C:28]1[CH:33]=[C:32]([SH:34])[CH:31]=[C:30]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:29]=1[OH:39])([CH3:27])[CH3:26]>ClCCl>[CH3:27][C:25]([C:28]1[CH:33]=[C:32]([S:34][CH2:3][CH2:2][C:1]([NH:7][CH2:8][C:9](=[O:10])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:4])[CH:31]=[C:30]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:29]=1[OH:39])([CH3:24])[CH3:26]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 13140Acryloyl chlorideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)

Product 1

HCID 14479946HCID 14479946, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloyl chloride (2 ml) was added to a cold (5°) solution of 2-aminoacetophenone hydrochloride (4.6 g, 27 mmole) and triethylamine (7 ml) in dichloromethane (25 ml) and the mixture was stirred at room temperature. An additional 7 ml of triethylamine was added. After one hour, 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (11 g, 46 mmole) was added and the mixture heated to reflux. The mixture was allowed to cool to room temperature and the reaction mixture was washed sequentially with 10% hydrochloric acid and water, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on silica gel and recrystallization from ethyl acetate gave the title compound, m.p. 146°-148°. Analysis. Calcd. for C25H33NO3S: C, 70.22; H, 7.78; N, 3.28; S, 7.22. Found: C, 69.95; H, 7.93; N, 3.20; S, 7.62.

Workup

  1. temperaturethe mixture heated to reflux
  2. temperatureto cool to room temperature
  3. washthe reaction mixture was washed sequentially with 10% hydrochloric acid and water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatography on silica gel and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2cacac95f6e14c0281a7ddc403a92ea5
Source dataset
uspto-grants-1991_11
Patent number
US05066679

Reaction notes

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