Water → 7-Fluoro-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 1687981Notes

Reaction equation

HRID 1687981 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12].[N-:13]=[N+]=[N-].[Na+].O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][CH2:6][NH:13][C:5](=[O:12])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 27332626-fluoro-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 552506527-Fluoro-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

6-Fluoro-chroman-4-one (539 mg, 3.24 mmol) was dissolved in Sulfuric acid (6.0 mL) and Sodium azide (258 mg, 3.97 mmol) was added at room temperature. The reaction was stirred for 30 h, then poured into water. The solids were collected by filtration, washing with 50 mL water. After drying, 7-Fluoro-3,4-dihydro-2H-b enzo[f][1,4]oxazepin-5-one was isolated as a white solid (395 mg, 67%). 1H-NMR (CDCl3): 7.65 (m, 1H), 7.15 (m, 1H), 7.01 (m, 1H), 6.74 (s, 1H),

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashing with 50 mL water
  3. customAfter drying

Sources & evidence

ORD record
ord-ef14633652604163aee6153a258b5739
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…