Diethyl Ether → HCID 86613736, compound

HRID 40458

Reaction equation

HRID 40458 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C(N(CC)CC)C.[F:12][C:13]1[C:18]([C:19](Cl)=[O:20])=[C:17]([F:22])[C:16]([F:23])=[C:15]([F:24])[C:14]=1[F:25].CC[O:28]CC>>[F:12][C:13]1[C:18]([C:19]([OH:28])=[O:20])=[C:17]([F:22])[C:16]([F:23])=[C:15]([F:24])[C:14]=1[F:25].[F:12][C:13]1[C:18]([C:19]([OH:28])=[O:20])=[C:17]([F:22])[C:16]([F:23])=[C:15]([F:24])[C:14]=1[F:25].[CH2:1]([NH2:4])[CH2:2][NH2:3]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 3301EthylenediamineHCID 8471TriethylamineHCID 75256Pentafluorobenzoyl chloride

Product 1

HCID 86613736HCID 86613736, compound

Procedure

Ethylene diamine (130 mg, 2.1 mmol) and triethylamine (510 mg, 5.0 mmol), together dissolved in 10 mL anhydrous ether is added to pentafluorobenzoyl chloride (1.2 g, 5.0 mmol) in 10 mL anhydrous ether. White precipitate is obtained and filtered off. The residue is washed with chloroform, then water and then filtered to recover ethylene diamine bis(pentafluorobenzoate) (III) as white needle crystals (yield, 100%). Sodium azide (270 mg, 4.2 mmol) in 1.7 mL water and 4.0 mL DMF is then reacted with III (870 mg, 2.0 mmol) in 20 mL DMF, and stirred overnight on a 60° C. hotplate. A white precipitate is obtained. The solution is reduced to half-volume by evaporation and the precipitate is filtered off (yield, 35%), dried and recrystallised from DMF to give ethylene diamine bis(4-azido-2,3,5,6-tetrafluorobenzoate) (IV) as white crystals. FTIR: 2129 (N3 asymmetric stretch), 1666 (C═O stretch), 1554, 1483, 1242 (N3 symmetric stretch), no acid OH band at 3000-3500.

Workup

  1. customWhite precipitate is obtained
  2. filtrationfiltered off
  3. washThe residue is washed with chloroform
  4. filtrationwater and then filtered
  5. customto recover

Sources & evidence

ORD record
ord-133a7ea9ff03486ea4b88148682a818d
Source dataset
uspto-grants-2013_09
Patent number
US08530269B2

Linked notes

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