Diethylamine → HCID 131711466, compound

HRID 614857Notes

Reaction equation

HRID 614857 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17]Cl)=[CH:12][C:11]=3[C:7]=2[CH:6]=1)=[O:4].[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23]>O1CCCC1>[OH2:4].[ClH:1].[ClH:1].[CH2:22]([N:24]([CH2:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][N:24]([CH2:25][CH3:26])[CH2:22][CH3:23])=[CH:12][C:11]=3[C:7]=2[CH:6]=1)=[O:4])[CH2:25][CH3:26])[CH3:23].[CH2:22]([N:24]([CH2:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][N:24]([CH2:25][CH3:26])[CH2:22][CH3:23])=[CH:12][C:11]=3[C:7]=2[CH:6]=1)=[O:4])[CH2:25][CH3:26])[CH3:23].[ClH:1].[ClH:1]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 12331792HCID 12331792, compound

Product 1

HCID 131711466HCID 131711466, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 25.0 g (0.078 mole) of 2,8-bis(chloroacetyl)dibenzofuran and 100 ml of tetrahydrofuran, cooled in an ice/water bath, was added 100 ml of diethylamine over a 20 minute period. The mixture was refluxed gently for 24 hours then filtered while hot. The solvent was removed in vacuo, and the remaining residue was slurried with ether and filtered. The filtrate was treated with ethereal HCl to give the desired product which was recrystallized from methanol-ether then from ethanol-ether. M.P. 225°-227° C. (dec), λmaxH2O 254, E1cm1% 1250.

Workup

  1. temperaturecooled in an ice/water bath
  2. temperatureThe mixture was refluxed gently for 24 hours
  3. filtrationthen filtered while hot
  4. customThe solvent was removed in vacuo
  5. filtrationfiltered
  6. additionThe filtrate was treated with ethereal HCl

Sources & evidence

ORD record
ord-854a1d2e57d440b6b86449bf261c3fe7
Source dataset
uspto-grants-1979_03
Patent number
US04146624

Reaction notes

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