Pyridine → HCID 15220889, compound

HRID 1033718Notes

Reaction equation

HRID 1033718 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([S:15](Cl)(=[O:17])=[O:16])[CH:8]=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)=[O:4].N1C=CC=CC=1.[NH2:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH:28]=[CH:29][C:30]([C:37](=[O:53])[NH:38][C:39]1[CH:44]=[C:43]([S:45]([OH:48])(=[O:47])=[O:46])[CH:42]=[C:41]([S:49]([OH:52])(=[O:51])=[O:50])[CH:40]=1)=[C:31]2[OH:36].CN(C)C(=O)C>C(O)C>[C:3]([C:5]1[CH:6]=[C:7]([S:15]([NH:25][C:26]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:27]=2[CH:28]=[CH:29][C:30]([C:37](=[O:53])[NH:38][C:39]2[CH:44]=[C:43]([S:45]([OH:48])(=[O:47])=[O:46])[CH:42]=[C:41]([S:49]([OH:52])(=[O:51])=[O:50])[CH:40]=2)=[C:31]3[OH:36])(=[O:17])=[O:16])[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=1)([OH:2])=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31374DimethylacetamideHCID 37891971,3-Benzenedicarboxylic acid, 5-(chlorosulfonyl)-, 1,3-dimethyl esterHCID 15220888HCID 15220888, compound

Product 1

HCID 15220889HCID 15220889, compoundYield 121.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Dimethoxycarbonylbenzenesulfonyl chloride (1.9 grams) and 2 ml of pyridine were added to 2.7 grams of 5-amino-2-(3,5-disulfophenylcarbamoyl)-1-naphthol and 27 ml of N,N-dimethylacetamide. The mixture was stirred for 1 hour at room temperature and then 50 ml of ethyl alcohol were added, and the crystals which precipitated out were recovered by filtration. 30 ml of methyl alcohol, 2 grams of sodium hydroxide and 10 ml of water were added to the crystals and, after boiling under reflux for 1 hour, 5 grams of 5-(3,5-dicarboxyphenylsulfonamido)-2-(3,5-disulfophenylcarbamoyl)-1-naphthol were obtained.

Workup

  1. customthe crystals which precipitated out
  2. filtrationwere recovered by filtration
  3. addition30 ml of methyl alcohol, 2 grams of sodium hydroxide and 10 ml of water were added to the crystals
  4. temperatureunder reflux for 1 hour

Sources & evidence

ORD record
ord-a510160e324048d3aaaa0974fc087839
Source dataset
uspto-grants-1994_05
Patent number
US05312724

Reaction notes

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