Ethyl 3-aminobenzoate → HCID 8823771, compound

HRID 2241162Notes

Reaction equation

HRID 2241162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)(=[O:10])=[O:9])[CH:17]=1)[CH3:13]

Participants

4

Reactant 2

HCID 11400Ethyl 3-aminobenzoateHCID 179093-Chlorobenzenesulphonyl chloride

Product 1

HCID 8823771HCID 8823771, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 3-chloro-benzenesulfonyl chloride (2.68 g, 13.0 mmol) in toluene (10.0 ml) was warmed to 100° C. and treated with a solution of 3-amino-benzoic acid ethyl ester (2.00 g, 12.0 mmol) in toluene (10.0 ml). The mixture was stirred at 100° C. for 1 h, then cooled to 0° C. for 1 h. The precipitated solid was filtered, washing with toluene. Drying of the solid under high vacuum yielded 3-(3-chloro-benzenesulfonylamino)-benzoic acid ethyl ester (4.03 g, 98%) as an off-white solid, which was used crude in the following reaction.

Workup

  1. temperaturecooled to 0° C. for 1 h
  2. filtrationThe precipitated solid was filtered
  3. washwashing with toluene
  4. customDrying of the solid under high vacuum

Sources & evidence

ORD record
ord-a28be2e7613044cfb7df5446eb3e5c96
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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