Sodium Azide → HCID 86613735, compound

HRID 40459Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:15])[C:9]([F:16])=[C:8](F)[C:7]=1[F:18].[F:19][C:20]1[C:25]([C:26]([OH:28])=[O:27])=[C:24]([F:29])[C:23]([F:30])=[C:22](F)[C:21]=1[F:32].[CH2:33]([NH2:36])[CH2:34][NH2:35]>O.CN(C=O)C>[N:1]([C:8]1[C:7]([F:18])=[C:6]([F:5])[C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:15])[C:9]=1[F:16])=[N+:2]=[N-:3].[N:1]([C:22]1[C:21]([F:32])=[C:20]([F:19])[C:25]([C:26]([OH:28])=[O:27])=[C:24]([F:29])[C:23]=1[F:30])=[N+:2]=[N-:3].[CH2:33]([NH2:36])[CH2:34][NH2:35]

Participants

Conditions

Temperature: 60 °C

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

customA white precipitate is obtained
customThe solution is reduced to half-volume by evaporation
filtrationthe precipitate is filtered off
custom(yield, 35%)
customdried
customrecrystallised from DMF

Sources & evidence

ORD record: ord-4f4d911606974fc19e7b8117ef584f02
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530269B2

Reaction notes

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