Triethylamine hydrochloride → 2-(4-Nitro-phenyl)-5-[3-(2H-tetrazol-5-yl)-propyl]-4-thioxo-4,5-dihydro-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-6-one

HRID 1713045Notes

Reaction equation

HRID 1713045 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl.C(N(CC)CC)C.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][C:24]3[CH:25]=[C:26]4[C:32](=[O:33])[N:31]([CH2:34][CH2:35][CH2:36][C:37]#[N:38])[C:30](=[S:39])[N:27]4[C:28]=3[CH:29]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]>COCCOC>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([C:22]2[O:23][C:24]3[CH:25]=[C:26]4[C:32](=[O:33])[N:31]([CH2:34][CH2:35][CH2:36][C:37]5[N:1]=[N:2][NH:3][N:38]=5)[C:30](=[S:39])[N:27]4[C:28]=3[CH:29]=2)=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 116537784-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyronitrile

Product 1

HCID 115319112-(4-Nitro-phenyl)-5-[3-(2H-tetrazol-5-yl)-propyl]-4-thioxo-4,5-dihydro-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-6-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium azide (76 mg, 1.17 mmol) and triethylamine hydrochloride (161 mg, 1.17 mmol) are added to a solution of Compound 35 (462.5 mg, 1.25 mmol) dissolved in DME (15 ml) and the suspension is refluxed for 48 hours. The mixture is then cooled to room temperature and the solvent is removed under reduced pressure. Water (30 ml) and ethyl acetate (30 ml) are added thereto and the aqueous phase is extracted three more times with ethyl acetate. The combined organic extracts are dried over Na2SO4 and the solvent is evaporated under reduced pressure. The crude product is recrystallized from ethanol to give Compound 36.

Workup

  1. temperaturethe suspension is refluxed for 48 hours
  2. customthe solvent is removed under reduced pressure
  3. additionWater (30 ml) and ethyl acetate (30 ml) are added
  4. extractionthe aqueous phase is extracted three more times with ethyl acetate
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. customthe solvent is evaporated under reduced pressure
  7. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-98273622fff54d2884ef0b310bf74c98
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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