tert-Butyl methyl ether → HCID 66665401, compound

HRID 221766Notes

Reaction equation

HRID 221766 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:16]([F:19])([F:18])[F:17])[CH2:14][CH2:13][O:12][CH2:11][C:10]([NH2:15])=[N:9]1.[N+:20]([O-])([O-:22])=[O:21].[K+].CC(OC)(C)C>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:20]([O-:22])=[O:21])=[CH:4][C:3]=1[C:8]1([C:16]([F:19])([F:17])[F:18])[CH2:14][CH2:13][O:12][CH2:11][C:10]([NH2:15])=[N:9]1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24434Potassium NitrateHCID 66665831HCID 66665831, compound

Product 1

HCID 66665401HCID 66665401, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5-(2-fluoro-phenyl)-5-trifluoromethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine (1.12 g, 4.05 mmol) in 12 mL concentrated sulfuric acid (95%) was added potassium nitrate (533 mg, 5.27 mmol) in two portions. The reaction mixture was stirred at rt for 30 minutes, it was then poured onto ice water and TBME was added. The layers were separated, washed with water and TBME. The combined aqueous layers were basified with solid Na2CO3 and extracted with EtOAc. The EtOAc layers were dried over MgSO4.H2O and evaporated to give 1.29 g of the title compound was a white solid.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. washwashed with water and TBME
  4. extractionextracted with EtOAc
  5. dry with materialThe EtOAc layers were dried over MgSO4.H2O
  6. customevaporated

Sources & evidence

ORD record
ord-54416ca1459c4cdf818cd5883c589443
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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