Tert-Butyl nitrite → HCID 21862832, compound

HRID 1415766Notes

Reaction equation

HRID 1415766 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][C:3]=1[C:24]([O:26][CH3:27])=[O:25].N(OC(C)(C)C)=O>O1CCCC1>[F:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[CH:2]=[C:3]([C:24]([O:26][CH3:27])=[O:25])[CH:4]=[C:5]2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 21862757HCID 21862757, compound

Product 1

HCID 21862832HCID 21862832, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.00 g (5.2 mmol) of 5-amino-1-(4-fluorophenyl)-4-methoxycarbonyl-2-(4-methylsulfonylphenyl)pyrrole [prepared as described in step (ii) above] were dissolved in 50 ml of anhydrous tetrahydrofuran, and 6.38 g (61.8 mmol) of t-butyl nitrite were added to the resulting solution at room temperature and under a nitrogen atmosphere. The mixture was then stirred at room temperature for 30 minutes, after which it was heated under reflux for 2 hours. The solvent was then removed by distillation under reduced pressure and the residue was applied to a silica gel chromatography column and eluted with a 2:3 by volume mixture of ethyl acetate and hexane, to give 1.30 g (yield 68%) of the title compound as a yellow powder, melting at 144-146° C.

Workup

  1. temperatureafter which it was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was then removed by distillation under reduced pressure
  4. washeluted with a 2:3 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5a9be1e5374144adbd9f5eb18e00ba88
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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