Citric Acid → HCID 67120728, compound

HRID 2365577Notes

Reaction equation

HRID 2365577 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.[C:14]1([S:24](Cl)(=[O:26])=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(C)=O.CCOCC.C1(C)C=CC=CC=1>[C:14]1([S:24]([NH:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:12][CH:13]=2)(=[O:26])=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 655264-(Aminomethyl)Benzoic AcidHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 67120728HCID 67120728, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

4 N NaOH solution (30 ml) is added to a suspension of 4-(aminomethyl)benzoic acid (5.01 g, 31.82 mmol) in acetone (100 ml). Toluene (100 ml) is added and the reaction is heated at 40° C. to obtain dissolution. The solution is cooled to 0° C. and treated with 1-naphthalene sulfonyl chloride (12 g, 51.35 mmol) in acetone (100 ml) and the resulting reaction mixture is stirred for 3 hours. The reaction is acidified using citric acid and concentrated in vacuo. The residue is taken up in EtOAc and washed with water. The aqueous layer is back extracted with EtOAc and the combined organic layers are washed with water, brine, dried (Na2SO4) and the solvent removed in vacuo to yield a light brown solid. Trituration with Et2O yields the title compound.

Workup

  1. customto obtain
  2. dissolutiondissolution
  3. temperatureThe solution is cooled to 0° C.
  4. customthe resulting reaction mixture
  5. concentrationconcentrated in vacuo
  6. washwashed with water
  7. extractionThe aqueous layer is back extracted with EtOAc
  8. washthe combined organic layers are washed with water, brine
  9. dry with materialdried (Na2SO4)
  10. customthe solvent removed in vacuo
  11. customto yield a light brown solid

Sources & evidence

ORD record
ord-0f784daa2fcb4fe69c468d7f8ef9d9c0
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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