Sulfuric Acid → 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

HRID 488377Notes

Reaction equation

HRID 488377 reaction equation
[N-:1]=[N+]=[N-].[Na+].S(=O)(=O)(O)O.[CH2:10]1[CH2:20][C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1>O.C(Cl)(Cl)Cl>[NH:1]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10][CH2:20][C:18]1=[O:19]

Participants

6

Reactant 3

HCID 1118Sulfuric Acid2×HCID 107241-TetraloneHCID 33557Sodium Azide

Product 1

HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A solution of sodium azide (25 g, 370 mmol) in water (13 mL) and chloroform (160 mL) is cooled to 0° C. and treated dropwise with concentrated sulfuric acid (11 mL). Stirring is continued for 30 min and the layers separated. The organic layer is dried over anhydrous sodium sulfate, filtered, and α-tetralone (20 g, 137 mmol) is added in one protion with stirring. The resulting solution is heated at 40° C. and concentrated sulfuric acid (38 mL) is added dropwise to maintain the internal temperature at 40-45° C. and stirring continued for 1 h, then cooled to 20° C. and poured into a sepratory funnel. The bottom layer is added dropwise with stirring to ise water (900 mL). The resulting solids are collected by filtration, and dried in vacuo at 40° C. to give 19.7 g of an off-white solid (89%), mp 139-140° C.; MS (ESI+) m/z 162 (M+H).

Workup

  1. customthe layers separated
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. stirringwith stirring
  5. temperatureto maintain the internal temperature at 40-45° C.
  6. stirringstirring
  7. waitcontinued for 1 h
  8. temperaturecooled to 20° C.
  9. additionpoured into a sepratory funnel
  10. additionThe bottom layer is added dropwise
  11. stirringwith stirring
  12. filtrationThe resulting solids are collected by filtration
  13. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-46c92d4f980c42cfb312b626d2f707e3
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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