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

HRID 1041639Notes

Reaction equation

HRID 1041639 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-1866d587c9ae4622b3adac6152a08c69
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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