Sulfuric Acid → HCID 12318584, compound

HRID 1287594Notes

Reaction equation

HRID 1287594 reaction equation
[Li+].[AlH4-].S(=O)(=O)(O)O.[C:8]([N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([Br:22])=[CH:14][C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2)(=O)[CH3:9].[OH-].[Na+]>O1CCCC1.O>[Br:22][C:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:11]([CH2:8][CH3:9])[C:12]2[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=2[CH:14]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 5409015-acetyl-10-bromo-5H-dibenz[b,f]azepine

Product 1

HCID 12318584HCID 12318584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

To 275 parts of a vigorously-stirred 31/2% solution of lithium tetrahydroaluminate(1-) in tetrahydrofuran at 0°-5° is slowly added 8 parts of concentrated sulfuric acid. The resultant mixture is stirred at 0°-5° for 1 hour, whereupon a solution of approximately 63 parts of 5-acetyl-10-bromo-5H-dibenz[b,f]azepine in 135 parts of tetrahydrofuran is stirred in during 30 minutes, producing a yellow color. The mixture thus obtained is stirred at 0°-5° for 30 minutes, whereupon a mixture of 20 parts of water and 35 parts of tetrahydrofuran, followed first by 40 parts of aqueous 25% sodium hydroxide and finally by 30 parts of water, are consecutively introduced. Insoluble solids are thereupon filtered out and washed with hot tetrahydrofuran, and the washings are combined with the filtrate. The resultant solution is dried over magnesium sulfate and stripped of solvent by vacuum distillation. The residual yellow solid, recrystallized from 2-propanol, affords 10-bromo-5-ethyl-5H-dibenz[b,f]azepine melting at approximately 147.5°-148.5°.

Workup

  1. customproducing a yellow color
  2. customThe mixture thus obtained
  3. additionare consecutively introduced
  4. filtrationInsoluble solids are thereupon filtered out
  5. washwashed with hot tetrahydrofuran
  6. dry with materialThe resultant solution is dried over magnesium sulfate
  7. distillationstripped of solvent by vacuum distillation
  8. customThe residual yellow solid, recrystallized from 2-propanol

Sources & evidence

ORD record
ord-b89d2d215cb948099e5664ddf3261116
Source dataset
uspto-grants-1976_10
Patent number
US03985730

Reaction notes

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