2-Naphthalenesulfonyl chloride → HCID 54510245, compound

HRID 2301276Notes

Reaction equation

HRID 2301276 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][NH2:10])[CH:4]=1.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[S:21](Cl)(=[O:23])=[O:22]>O1CCOCC1>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][NH:10][S:21]([C:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 151331,3-Benzenedimethanamine

Product 1

HCID 54510245HCID 54510245, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

α,α′-Diamino-m-xylene (24 g, 176 mmol) was dissolved in 50 ml 1,4-dioxane, and at 15-20° C. naphthalene-2-sulfonyl chloride (4 g, 17.6 mmol) dissolved in 50 ml of 1,4-dioxane was slowly added over 3 hours under stirring. Stirring was continued at RT. After standing overnight the formed precipitate was filtered off and the filtrate concentrated in vacuo. The residue was distributed between DCM and water. The organic layer was separated and washed with water and 1 N HCl. The oily layer formed between the organic and aqueous layer was separated. It solidified on standing. This solid material was treated with ethyl acetate, sucked off, and washed with ethyl acetate. The residue was dissolved in water and treated with potassium carbonate solution. The aqueous solution was extracted three times with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered, and concentrated to yield 3.2 g of the title compound. MS=327.3 (M+H)+.

Workup

  1. additionwas slowly added over 3 hours
  2. stirringStirring
  3. customwas continued at RT
  4. filtrationthe formed precipitate was filtered off
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe organic layer was separated
  7. washwashed with water and 1 N HCl
  8. customThe oily layer formed between the organic and aqueous layer
  9. customwas separated
  10. additionThis solid material was treated with ethyl acetate
  11. washwashed with ethyl acetate
  12. dissolutionThe residue was dissolved in water
  13. additiontreated with potassium carbonate solution
  14. extractionThe aqueous solution was extracted three times with ethyl acetate
  15. dry with materialthe combined organic phases were dried over magnesium sulfate
  16. filtrationfiltered
  17. concentrationconcentrated

Sources & evidence

ORD record
ord-c045a3340c1447e887d204ccab8a0001
Source dataset
uspto-grants-2002_12
Patent number
US06500803B1

Reaction notes

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