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Water → 2-t-Butyl-5-cyano-1-nitrobenzene

HRID 1637506
Notes
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Reaction equation

HRID 1637506 reaction equation
N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([C:30](=O)[NH2:31])=[CH:26][C:25]=1[N+:33]([O-:35])=[O:34])([CH3:23])([CH3:22])[CH3:21].O>O1CCCC1.CCCCCC>[C:20]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=1[N+:33]([O-:35])=[O:34])([CH3:23])([CH3:21])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 19348480HCID 19348480, compound

Product 1

HCID 107033622-t-Butyl-5-cyano-1-nitrobenzeneYield 96.5%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8058HexaneSolvent

Procedure

3.3 ml of pyridine and then 4.3 ml of trifluoroacetic anhydride were added to a solution of 2.25 g (10.1 mmol) of 2-t-butyl-5-carbamoyl-1-nitrobenzene [prepared as described in Preparation 38(i)] in 20 ml of tetrahydrofuran, and the resulting mixture was stirred for 20 minutes. The reaction mixture was then mixed with water, and the aqueous mixture was extracted with a mixture of ethyl acetate and hexane. The extract was washed with water and with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 50 g of silica gel to give 1.99 g (yield 96%) of the title compound as crystals, melting at 70.5-71.5° C. (from hexane).

Workup

  1. extractionthe aqueous mixture was extracted with a mixture of ethyl acetate and hexane
  2. washThe extract was washed with water and with a saturated aqueous solution of sodium chloride
  3. dry with materialafter which it was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography through 50 g of silica gel

Sources & evidence

ORD record
ord-ed162831756148d4a4cf3f435c2b23ac
Source dataset
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06040339

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes