Water → HCID 54241509, compound

HRID 1764548Notes

Reaction equation

HRID 1764548 reaction equation
[C:1]1([O:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1([S:36](Cl)(=[O:38])=[O:37])[C:27]2[C:22](=[CH:23][C:24]([S:28](Cl)(=[O:30])=[O:29])=[CH:25][CH:26]=2)[CH:21]=[C:20]([S:32](Cl)(=[O:34])=[O:33])[CH:19]=1.[OH2:40]>N1C=CC=CC=1>[C:1]1([O:7][S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][S:28]([C:24]3[CH:23]=[C:22]4[C:27](=[CH:26][CH:25]=3)[C:18]([S:36]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([S:8]([O:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:9])=[O:40])=[CH:16][CH:15]=3)(=[O:38])=[O:37])=[CH:19][C:20]([S:32]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([S:8]([O:7][C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)(=[O:9])=[O:10])=[CH:16][CH:15]=3)(=[O:34])=[O:33])=[CH:21]4)(=[O:30])=[O:29])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4426510phenyl 4-aminobenzenesulfonateHCID 1257361167294-61-5

Product 1

HCID 54241509HCID 54241509, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 11.2 g of the above amine in 50 ml of pyridine is added 6.35 g of 1,3,6-naphthalenetrisulfonyl chloride. The resulting solution is heated on a steam bath for one hour, cooled to room temperature and poured into cold water with separation of an oil. The mixture is extracted with methylene chloride. The methylene chloride extract is washed with 0.5N hydrochloric acid, then with water and dried over magnesium sulfate. The solvent is removed and the resulting oil is dissolved in benzene:acetone (7:3) and passed through a bed of magnesol on a sintered glass funnel. The cake is washed with additional benzene:acetone (7:3). The filtrate and washings are combined and evaporated and dried in vacuo to yield 11.9 g of the product of the example as a cream colored solid.

Workup

  1. temperatureThe resulting solution is heated on a steam bath for one hour
  2. extractionThe mixture is extracted with methylene chloride
  3. extractionThe methylene chloride extract
  4. washis washed with 0.5N hydrochloric acid
  5. dry with materialwith water and dried over magnesium sulfate
  6. customThe solvent is removed
  7. dissolutionthe resulting oil is dissolved in benzene:acetone (7:3)
  8. custompassed through a bed of magnesol on a sintered glass funnel
  9. washThe cake is washed with additional benzene:acetone (7:3)
  10. customevaporated
  11. customdried in vacuo

Sources & evidence

ORD record
ord-c6e6c38ba20b425cb9221184f1320a97
Source dataset
uspto-grants-1978_09
Patent number
US04117003

Reaction notes

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