Triethylamine → HCID 14479949, compound

HRID 973973Notes

Reaction equation

HRID 973973 reaction equation
Br[CH:2]([CH3:6])[C:3](Cl)=[O:4].Cl.[NH2:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].C(N(CC)CC)C.[CH3:25][C:26]([C:29]1[CH:34]=[C:33]([SH:35])[CH:32]=[C:31]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:30]=1[OH:40])([CH3:28])[CH3:27]>C(Cl)Cl>[CH3:28][C:26]([C:29]1[CH:34]=[C:33]([S:35][CH:2]([CH3:6])[C:3]([NH:8][CH2:9][C:10](=[O:11])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:4])[CH:32]=[C:31]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:30]=1[OH:40])([CH3:25])[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 979802-Bromopropanoyl chlorideHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)

Product 1

HCID 14479949HCID 14479949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Bromopropionyl chloride (5 mmole) is added to a cold (5° C.) solution of 2-aminoacetophenone hydrochloride (5 mmole) in methylene chloride followed by 14 ml of triethylamine in methylene chloride. The mixture is stirred at room temperature. After about 1 hour, the product of Example 2 is added and the solution heated to reflux. The mixture is allowed to cool to room temperature. The reaction mixture is treated as in Example 3 to produce 2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-(2-oxo-2-phenylethyl)propanamide.

Workup

  1. temperaturethe solution heated to reflux
  2. temperatureto cool to room temperature
  3. additionThe reaction mixture is treated as in Example 3

Sources & evidence

ORD record
ord-688bb3affea8437e9eee2540d4852d66
Source dataset
uspto-grants-1991_11
Patent number
US05066679

Reaction notes

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