Triethylamine → HCID 9909691, compound

HRID 2082296Notes

Reaction equation

HRID 2082296 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[NH:25][C:26](=[O:29])[CH:27]=[CH2:28].C(N(CC)CC)C>CO>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:11][CH2:28][CH2:27][C:26]([NH:25][C:19]2[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=2[CH3:17])=[O:29])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 13723638HCID 13723638, compound

Product 1

HCID 9909691HCID 9909691, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-bis-(1,1-Dimethylethyl)-4-mercaptophenol(1.19 g, 0.005 mole), N-(2,6-dimethylphenyl)-2-propenamide (0.87 g, 0.005 mole) and triethylamine (0.5 ml) in methanol (100 ml) were stirred at room temperature under argon for 12 hours. The solvent and triethylamine were removed on a rotary evaporator and the product purified by chromatography on silica. The solvents were removed and the product recrystallized from ethyl acetate/hexane, filtered and dried in vacuo to yield the title compound, m.p. ca. 142.5°-144° C.

Workup

  1. customThe solvent and triethylamine were removed on a rotary evaporator
  2. customthe product purified by chromatography on silica
  3. customThe solvents were removed
  4. customthe product recrystallized from ethyl acetate/hexane
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-83d64876b6a94a75b9cbdc7ac22f30b9
Source dataset
uspto-grants-1993_02
Patent number
US05189038

Reaction notes

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