Ethanol → HCID 87486712, compound

HRID 227286Notes

Reaction equation

HRID 227286 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].C(O)C.[CH3:15][CH:16]([NH:18][C:19]([CH3:24])([CH:21]([CH3:23])[CH3:22])[CH3:20])[CH3:17]>CCOCC>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[CH3:15][CH:16]([NH:18][C:19]([CH3:24])([CH:21]([CH3:23])[CH3:22])[CH3:20])[CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 10057607642407-44-1

Product 1

HCID 87486712HCID 87486712, compoundYield 892.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.60 g (3.5 mmole) anhydrous tosylic acid was dissolved in possibly as little as ethanol. Then a solution of 0.55 g (0.38 mmole) N-(1-methylethyl)-2,3-dimethyl-2-butylamine in 10 mL anhydrous ether was added dropwise with stirring. The mixture was stood overnight, and then distilled off the solvent. The residue was washed thoroughly with anhydrous ethanol to give a colorless solid 1.07 g, mp 119-120° C. 1H-NMR(D2O, ppm) 0.96(d, 6H, 2CH3), 1.303(s, 6H, 2CH3), 1.36(d, 6H, 2CH3), 2.02-2.15(m, 1H, C(H), 2.401(s, 3H, CH3), 3.62-3.73(m, 1H, CH), 7.38(d,2H, 2Ar—H), 7.70(d,2H, 2Ar—H).

Workup

  1. distillationdistilled off the solvent
  2. washThe residue was washed thoroughly with anhydrous ethanol

Sources & evidence

ORD record
ord-4c8e56ae23b34f36aa297348ef341d31
Source dataset
uspto-grants-2009_07
Patent number
US07560473B2

Reaction notes

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