tert-Butanol → HCID 54929897, compound

HRID 446614Notes

Reaction equation

HRID 446614 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.[C:26](O)([CH3:29])([CH3:28])[CH3:27]>>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([O:8][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54929897HCID 54929897, compoundYield 76%

Procedure

4-Amino-5-chloro-2-methoxybenzoic acid (1.0 g, 4.96 mmol) was dissolved in t-butanol (20 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.05 g, 5.46 mmol) was added with stirring at room temperature, and the mixture was stirred at room temperature under a nitrogen atmosphere for 17 hours. After the reaction was completed, the reaction mixture was filtered, and the filtrate was washed with hexane. The resulting filtrate was recrystallized with ethanol to give the title compound (0.97 g; yield, 76%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature under a nitrogen atmosphere for 17 hours
  2. filtrationthe reaction mixture was filtered
  3. washthe filtrate was washed with hexane
  4. customThe resulting filtrate was recrystallized with ethanol

Sources & evidence

ORD record
ord-4139410f12224f65b48eecc18b1ef64f
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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