Ammonia → 2-Naphthalenesulfonamide, 6,7-dihydroxy-

HRID 1390086Notes

Reaction equation

HRID 1390086 reaction equation
C([O:4][C:5]1[C:14]([O:15]C(=O)C)=[CH:13][C:12]2[C:7](=[CH:8][C:9]([S:19](Cl)(=[O:21])=[O:20])=[CH:10][CH:11]=2)[CH:6]=1)(=O)C.[NH3:23].[Na+].C(OC1C=C2C(=CC=1OC(=O)C)C=C(S([O-])(=O)=O)C=C2)(=O)C>O1CCCC1>[OH:4][C:5]1[C:14]([OH:15])=[CH:13][C:12]2[C:7](=[CH:8][C:9]([S:19]([NH2:23])(=[O:21])=[O:20])=[CH:10][CH:11]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 19832966HCID 19832966, compoundHCID 88763773HCID 88763773, compound

Product 1

HCID 1046752-Naphthalenesulfonamide, 6,7-dihydroxy-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20.0 g. (0.0583 mole) of 2,3-diacetoxy-7-naphthalenesulfonyl chloride in 300 ml. of tetrahydrofuran was treated with 8.7 ml. (0.13 mole) of aqueous 28% ammonia. The solid (9.9 g., infrared spectrum identical with that of 6,7-diacetoxy-2-naphthalenesulfonic acid sodium salt) was removed by filtration and the filtrate evaporated to dryness. The residue was dissolved in 150 ml. of ethyl acetate. The residue from evaporation of the dried (anhydrous sodium sulfate) solution was slurried with four 100-ml. portions of ether and then dissolved in 150 ml. of 3A alcohol. The solution was saturated with hydrogen chloride, allowed to stand overnight, and then concentrated at the water pump to give 9.7 g. of colorless residue. Recrystallization from 50 ml. of water gave 5.1 g. (37%) of pale violet solid, m.p. 218°-228° C.

Workup

  1. customwas removed by filtration
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue was dissolved in 150 ml
  4. customThe residue from evaporation of the
  5. dry with materialdried (anhydrous sodium sulfate) solution
  6. dissolutionportions of ether and then dissolved in 150 ml
  7. concentrationconcentrated at the water pump
  8. customto give 9.7 g
  9. customRecrystallization from 50 ml
  10. customof water gave 5.1 g

Sources & evidence

ORD record
ord-8b125dd17760463db9a759b96e1611dd
Source dataset
uspto-grants-1981_01
Patent number
US04247459

Reaction notes

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