Sulfuric Acid → 4[2{2(4-Sulfophenyl)ethylsulfonyl}4-nitrophenylazo]5-morpholinosulfonamido-1-naphthol

HRID 1390088Notes

Reaction equation

HRID 1390088 reaction equation
S(=O)(=O)(O)O.[N:6]([O-])=O.[Na+].[S:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][S:22]([C:25]2[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:26]=2[NH2:27])(=[O:24])=[O:23])=[CH:16][CH:15]=1)([OH:13])(=[O:12])=[O:11].[O:35]1[CH2:40][CH2:39][N:38]([S:41]([NH:44][C:45]2[CH:54]=[CH:53][CH:52]=[C:51]3[C:46]=2[CH:47]=[CH:48][CH:49]=[C:50]3[OH:55])(=[O:43])=[O:42])[CH2:37][CH2:36]1.C([O-])(=O)C.[Na+]>O.C(O)C.C(O)(=O)C>[S:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][S:22]([C:25]2[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:26]=2[N:27]=[N:6][C:47]2[C:46]3[C:51](=[CH:52][CH:53]=[CH:54][C:45]=3[NH:44][S:41]([N:38]3[CH2:39][CH2:40][O:35][CH2:36][CH2:37]3)(=[O:43])=[O:42])[C:50]([OH:55])=[CH:49][CH:48]=2)(=[O:23])=[O:24])=[CH:16][CH:15]=1)([OH:13])(=[O:12])=[O:11]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 202948662[2(4-Sulfophenyl)ethylsulfonyl]-4-nitroanilineHCID 202948755-Morpholinosulfonamido-1-naphtholHCID 23668193Sodium Nitrite

Product 1

HCID 1361093794[2{2(4-Sulfophenyl)ethylsulfonyl}4-nitrophenylazo]5-morpholinosulfonamido-1-naphthol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

To 3 ml. of conc. sulfuric acid under cooling was added 0.43 g. of sodium nitrite, dissolved by heating and, after cooling, 5.5 ml. of acetic acid were added thereto. The resulting solution was cooled to 5° C. and 2.32 g. of 2[2(4-sulfophenyl)ethylsulfonyl]-4-nitroaniline were added thereto with stirring. Stirring was continued at room temperature for 3 hours to prepare a diazonium salt solution. Separately, a solution of 1.85 g. of 5-morpholinosulfonamido-1-naphthol in 250 ml. of ethanol and 30 ml. of water was prepared, and a solution of 15 g. of sodium acetate in 40 ml. of water was added thereto with stirring. To the resulting solution, the diazonium salt solution as prepared above was added dropwise under ice-cooling. The reaction mixture was stirred at about 50° C. for 2 hours. Thereafter, the mixture was concentrated to about 100 ml., the precipitate thus separated was recovered by filtration and dried to give 4.3 g. of the desired product.

Workup

  1. additionwas added 0.43 g
  2. temperatureby heating
  3. temperatureafter cooling
  4. stirringStirring
  5. stirringwith stirring
  6. additionabove was added dropwise under ice-
  7. temperaturecooling
  8. stirringThe reaction mixture was stirred at about 50° C. for 2 hours
  9. concentrationThereafter, the mixture was concentrated to about 100 ml
  10. custom, the precipitate thus separated
  11. filtrationwas recovered by filtration
  12. customdried
  13. customto give 4.3 g

Sources & evidence

ORD record
ord-4b9cac2f78474071ac80be99cc349107
Source dataset
uspto-grants-1981_01
Patent number
US04247629

Reaction notes

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