Phosphoric Acid → HCID 136408876, compound

HRID 2198572Notes

Reaction equation

HRID 2198572 reaction equation
[N:1]([O-])=O.[Na+].S(=O)(=O)(O)O.P(=O)(O)(O)O.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][C:17]=1[S:26]([CH3:29])(=[O:28])=[O:27].[S:30]([C:34]1[CH:35]=[C:36]([CH:52]=[CH:53][CH:54]=1)[NH:37][NH:38][C:39]([C:41]1[CH:50]=[CH:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]=1[OH:51])=[O:40])([OH:33])(=[O:32])=[O:31]>[OH-].[Na+].C(O)(=O)C>[S:30]([C:34]1[CH:35]=[C:36]([CH:52]=[CH:53][CH:54]=1)[NH:37][NH:38][C:39]([C:41]1[CH:50]=[C:49]([N:1]=[N:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:18][C:17]=2[S:26]([CH3:29])(=[O:28])=[O:27])[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]=1[OH:51])=[O:40])([OH:33])(=[O:31])=[O:32]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 459387HCID 459387, compoundHCID 23668193Sodium NitriteHCID 54242380HCID 54242380, compound

Product 1

HCID 136408876HCID 136408876, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

1.5 g of sodium nitrite was added to 10 ml of concentrated sulfuric acid and the mixture was heated at 70° C. with stirring. After stirring for 30 minutes, the mixture was cooled to 0° C. and 20 ml of acetic acid and 6 ml of a 85% phosphoric acid were added thereto. Then 5.0 g of 1-amino-2,4-dimethanesulfonylbenzene was added to the mixture at below 5° C. and the mixture was stirred for 3 hours. After adding 40 ml of ice water to the solution, a solution containing 6.5 g of 2-(N-3-sulfoanilinocarbamoyl)-1-naphthol obtained in Step (1) of Synthesis Example 4 above dissolved in 20 ml of a 2% aqueous sodium hydroxide solution was added dropwise at below 5° C. The mixture was stirred at below 5° C. for 1 hour. The crystals thus-precipitated were collected by filtration and washed with 50 ml of acetonitrile.

Workup

  1. stirringAfter stirring for 30 minutes
  2. temperaturethe mixture was cooled to 0° C.
  3. stirringthe mixture was stirred for 3 hours
  4. additiona solution containing
  5. additionwas added dropwise at below 5° C
  6. stirringThe mixture was stirred at below 5° C. for 1 hour
  7. customThe crystals thus-precipitated
  8. filtrationwere collected by filtration
  9. washwashed with 50 ml of acetonitrile

Sources & evidence

ORD record
ord-4d2c9590c6c34dc396173c4ed7c9dfdd
Source dataset
uspto-grants-1982_11
Patent number
US04358526

Reaction notes

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