Hydrochloric Acid → 2,7-Bis[3-(diethylamino)propionyl]xanthene dihydrochloride hydrate

HRID 1076906Notes

Reaction equation

HRID 1076906 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([C:20](=[O:24])[CH2:21][CH2:22]Cl)=[CH:13][CH:14]=3)[CH2:9][C:8]=2[CH:7]=1)=[O:5].[I-].[K+].[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28].[ClH:32]>O1CCCC1>[OH2:5].[ClH:1].[ClH:32].[CH2:27]([N:29]([CH2:30][CH3:31])[CH2:2][CH2:3][C:4]([C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([C:20](=[O:24])[CH2:21][CH2:22][N:29]([CH2:30][CH3:31])[CH2:27][CH3:28])=[CH:13][CH:14]=3)[CH2:9][C:8]=2[CH:7]=1)=[O:5])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 8021DiethylamineHCID 123402792,7-Bis(3-chloropropionyl)xanthene

Product 1

HCID 215385612,7-Bis[3-(diethylamino)propionyl]xanthene dihydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 18.2 g (0.05 mole) of 2,7-bis(3-chloropropionyl)xanthene, 2 g of potassium iodide, 100 ml. of diethylamine and 100 ml. of tetrahydrofuran was allowed to stand for 3 days then filtered. The filtrate was evaporated to dryness leaving a residue which was treated with 10% HCl and filtered. The filtrate was made alkaline, extracted with methylene chloride and treated with ethereal HCl. The resulting precipitate was filtered, recrystallized from methanol-diethyl ether and hydrated in a constant humidity chamber to give the desired product. M.P. 184.5°-185.5°C.

Workup

  1. filtrationthen filtered
  2. customThe filtrate was evaporated to dryness
  3. customleaving a residue which
  4. filtrationfiltered
  5. extractionextracted with methylene chloride
  6. additiontreated with ethereal HCl
  7. filtrationThe resulting precipitate was filtered
  8. customrecrystallized from methanol-diethyl ether and hydrated in a constant humidity chamber

Sources & evidence

ORD record
ord-97eb3458f2fe4ada8fc1e18c69aa4d01
Source dataset
uspto-grants-1976_05
Patent number
US03957989

Reaction notes

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