Phosphoric Acid → HCID 136408875, compound

HRID 2198571Notes

Reaction equation

HRID 2198571 reaction equation
S(=O)(=O)(O)O.[N:6]([O-])=O.[Na+].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:54]=[CH:53][C:37]([NH:38][NH:39][C:40]([C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43]=2[OH:52])=[O:41])=[CH:36][CH:35]=1)([OH:33])(=[O:32])=[O:31]>[OH-].[Na+].C(O)(=O)C>[S:30]([C:34]1[CH:35]=[CH:36][C:37]([NH:38][NH:39][C:40]([C:42]2[CH:51]=[C:50]([N:6]=[N:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:18][C:17]=3[S:26]([CH3:29])(=[O:28])=[O:27])[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43]=2[OH:52])=[O:41])=[CH:53][CH:54]=1)([OH:33])(=[O:31])=[O:32]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 459387HCID 459387, compoundHCID 23668193Sodium NitriteHCID 54219924HCID 54219924, compound

Product 1

HCID 136408875HCID 136408875, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

To 10 ml of concentrated sulfuric acid, 1.5 g of sodium nitrite was added 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 at below 5° C. thereto and the mixture was stirred for 3 hours. After adding 40 ml of ice water, a solution containing 6.5 g of 2-(N-4-sulfoanilinocarbamoyl)-1-naphthol obtained in Step (1) of Synthesis Example 3 above dissolved in 20 ml of a 2% aqueous sodium hydroxide was added dropwise to the mixture and 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 to the mixture
  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-f2de406968154755a6d4e0ebd95ee49d
Source dataset
uspto-grants-1982_11
Patent number
US04358526

Reaction notes

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