Triethylamine → 2,5-Dichloro-N'-[(9,9-dioctyl-9H-fluoren-2-yl)carbonyl]benzohydrazide

HRID 11184Notes

Reaction equation

HRID 11184 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].C(N(CC)CC)C.[CH2:20]([C:28]1([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:40]2[CH:39]=[C:38]([C:41](Cl)=[O:42])[CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>ClCCCl.CCCCCCC>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([NH:6][NH:7][C:41]([C:38]1[CH:37]=[CH:36][C:35]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:40]=2[CH:39]=1)=[O:42])=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1442462,5-DichlorobenzhydrazideHCID 21982108HCID 21982108, compound

Product 1

HCID 219820882,5-Dichloro-N'-[(9,9-dioctyl-9H-fluoren-2-yl)carbonyl]benzohydrazide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8900HeptaneSolvent

Procedure

2,5-Dichlorobenzohydrazide (one equivalent) and triethylamine (one equivalent) were warmed in 500 mL of 1,2-dichloroethane until the solid material had dissolved. On cooling, 9,9-dioctyl-9H-fluorene-2-carbonyl chloride (one equivalent) was added and the mixture stirred at RT for two days. The insolubles were filtered off and the filtrate evaporated to give an oil. This was taken up in heptane and the precipitated solid filtered off. The remaining solution was dried (MgSO4) and concentrated to give the desired intermediate.

Workup

  1. dissolutionhad dissolved
  2. temperatureOn cooling
  3. filtrationThe insolubles were filtered off
  4. customthe filtrate evaporated
  5. customto give an oil
  6. filtrationthe precipitated solid filtered off
  7. dry with materialThe remaining solution was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6b6dfbab97d24624aa2762b3813fda4c
Source dataset
uspto-grants-2006_08
Patent number
US07094902B2

Reaction notes

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