Diethylamine → HCID 20312739, compound

HRID 2420059Notes

Reaction equation

HRID 2420059 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[C:21]2[C:12](=[CH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26]Cl)[CH:11]=[CH:10][CH:9]=1)=[O:7].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>O1CCCC1>[CH2:29]([N:31]([CH2:32][CH3:33])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[C:21]2[C:12](=[CH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])[CH:11]=[CH:10][CH:9]=1)=[O:7])[CH3:30]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 20312748HCID 20312748, compound

Product 1

HCID 20312739HCID 20312739, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

In each of four Carius tubes is placed 10 g of 1,5-bis(5-chlorovaleryl)anthracene (0.024 mole), 80 ml of diethylamine and 40 ml of tetrahydrofuran. The tubes are heated to 110° C. for 30 hours, cooled and their contents combined. The volatile components are evaporated in vacuo and the residue is slurried with 400 ml of chloroform. The organic phase is extracted twice with 100 ml portions of water, and two additional times with 100 ml portions of 10% HCl solution. The combined acid extracts are neutrallized using a cold 50% sodium hydroxide solution and reextracted with two 100 ml portions of chloroform. The combined chloroform extracts are dried over magnesium sulfate, filtered, evaporated to dryness and the residue is crystallized from n-heptane to give 36 g of 1,5-bis(5-diethylaminovaleryl)anthracene having a m.p. of 65°-7° C.

Workup

  1. temperaturecooled
  2. customThe volatile components are evaporated in vacuo
  3. extractionThe organic phase is extracted twice with 100 ml portions of water, and two additional times with 100 ml portions of 10% HCl solution
  4. dry with materialThe combined chloroform extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customthe residue is crystallized from n-heptane

Sources & evidence

ORD record
ord-71e174ed7ee0466da6679093079a570e
Source dataset
uspto-grants-1978_08
Patent number
US04108896

Reaction notes

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