Thionyl Chloride → Bis(3-di-n-butylaminopropyl)xanthene-2,7-dicarboxylate dihydrochloride

HRID 1076823Notes

Reaction equation

HRID 1076823 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:18]([OH:20])=[O:19].S(Cl)([Cl:23])=O.[CH2:25]([N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32]O)[CH2:26][CH2:27][CH3:28]>N1C=CC=CC=1.C1C=CC=CC=1.C(Cl)Cl>[ClH:23].[ClH:23].[CH2:25]([N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][O:16][C:15]([C:10]1[CH:9]=[CH:8][C:7]2[O:6][C:5]3[C:14](=[CH:1][C:2]([C:18]([O:20][CH2:32][CH2:31][CH2:30][N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])=[CH:3][CH:4]=3)[CH2:13][C:12]=2[CH:11]=1)=[O:17])[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 749051-Propanol, 3-(dibutylamino)-HCID 12340268Xanthene-2,7-dicarboxylic acid

Product 1

HCID 12340270Bis(3-di-n-butylaminopropyl)xanthene-2,7-dicarboxylate dihydrochlorideYield 31.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 23443464Methane, dichloro-, compd. with benzene (1:1)Solvent

Procedure

To 17.4 g (0.06 mole) of xanthene-2,7-dicarboxylic acid was added 100 ml (1.4 moles) of thionyl chloride and 4 drops of pyridine. The resulting solution was refluxed for four hours and solvent and excess thionyl chloride were removed. The intermediate diacid chloride in benzene-methylene chloride was reacted with 24 g (0.13 mole) of 3-di-n-butylamino-1-propanol by refluxing for three hours. Most of the solvent was removed and the residue allowed to stand for two days. The residue was diluted with methylene chloride and 10% hydrochloric acid. The organic layer and two methylene chloride washings of the aqueous layer were combined and dried over anhydrous magnesium sulfate. The solution was filtered and concentrated at reduced pressure to a solid residue. This was purified from isopropanol to give 12.9 g (29.6%) of bis(3-di-n-butylaminopropyl)xanthene-2,7-dicarboxylate dihydrochloride. M.P. 187.5°-190°C.

Workup

  1. temperatureThe resulting solution was refluxed for four hours
  2. customsolvent and excess thionyl chloride were removed
  3. temperatureby refluxing for three hours
  4. customMost of the solvent was removed
  5. additionThe residue was diluted with methylene chloride and 10% hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated at reduced pressure to a solid residue
  9. customThis was purified from isopropanol

Sources & evidence

ORD record
ord-2321398eeec549dd8a23dc6f9b73b3d4
Source dataset
uspto-grants-1976_05
Patent number
US03957986

Reaction notes

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