Lactic Acid → 1-Carboxyethyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

HRID 2057667Notes

Reaction equation

HRID 2057667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[C:31]([OH:36])(=[O:35])[CH:32]([CH3:34])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH:32]([C:31]([OH:36])=[O:35])[CH3:34])=[O:27])=[CH:29][CH:30]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 69252-Methylbenzenesulfonic acidHCID 203309694-[13-(4-Chlorophenyl)-12-tridecynylamino]benzoic acid

Product 1

HCID 203310091-Carboxyethyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask containing 10.0 g. 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoic acid, 3.3 g. lactic acid, 500 mg. toluene sulfonic acid and 500 ml. toluene is equipped with a Soxhlet extractor charged with activated 4A Linde molecular sieves. The solution is refluxed for 24 hours during which time the Soxhlet extractor is charged twice more with fresh sieves. The hot solution is filtered and left to cool, whereupon 1-carboxyethyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]-benzoate separates as off-white crystals.

Workup

  1. additionA flask containing 10.0 g
  2. additioncharged
  3. temperatureThe solution is refluxed for 24 hours during which time the Soxhlet extractor
  4. additionis charged twice more with fresh sieves
  5. filtrationThe hot solution is filtered
  6. waitleft
  7. temperatureto cool, whereupon 1-carboxyethyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]-benzoate

Sources & evidence

ORD record
ord-e7c6d8fe5be64174b6f1aa06388c89ab
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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