Methyl 4-Amino-2-chlorobenzoate → HCID 67395066, compound

HRID 1023737Notes

Reaction equation

HRID 1023737 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[S:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>>[Cl:15][C:16]1[CH:25]=[C:24]([NH:26][C:12]([C:6]2[S:7][C:8]([CH:9]([CH3:10])[CH3:11])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=2)=[O:14])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

3

Reactant 2

HCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 58420519HCID 58420519, compound

Product 1

HCID 67395066HCID 67395066, compoundYield 34.2%

Procedure

In the same manner as that of Example 24, 4,5-diisopropylthiophene-2-carboxylic acid (80 mg, 0.377 mmol) and methyl 2-chloro-4-aminobenzoate (126 mg, 0.679 mmol) were condensed, the reaction mixture was treated in a conventional manner, and then the residue was purified by silica gel chromatography [n-hexane-ethyl acetate (40:1)] and recrystallized to obtain methyl 2-chloro-4-[(4,5-diisopropylthiophene-2-carbonyl)amino]benzoate (49 mg, 34%) as colorless prisms.

Workup

  1. customcondensed
  2. additionthe reaction mixture was treated in a conventional manner
  3. customthe residue was purified by silica gel chromatography [n-hexane-ethyl acetate (40:1)]
  4. customrecrystallized

Sources & evidence

ORD record
ord-239898ba6b2941e4bc71ff5b4c17b86f
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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