tert-Butanol → tert-Butyl 4-(methylamino)benzoate

HRID 446532Notes

Reaction equation

HRID 446532 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[CH:5][CH:4]=1.Cl.C(N=C=NCCCN(C)C)C.[C:24](O)([CH3:27])([CH3:26])[CH3:25]>CN(C)C1C=CN=CC=1>[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69332534-(Methylamino)benzoate

Product 1

HCID 22291264tert-Butyl 4-(methylamino)benzoateYield 78%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-(Methylamino)benzoate (2.00 g, 13.2 mmol) was dissolved in tert-butanol (66 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (89 mg, 0.464 mmol) and 4-dimethylaminopyridine (81 mg, 0.660 mmol) were added, and the mixture was stirred at room temperature for 17 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1, v/v) to give the title compound (2.14 g; yield, 78%) as a yellow oily substance.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-34e95d34a9ec49d99e6c07421a7ecd6a
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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