Water → HCID 21505296, compound

HRID 1287602Notes

Reaction equation

HRID 1287602 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](OCC)=O)[C:10]2[CH:23]=[CH:24][CH:25]=[CH:26][C:9]=2[CH:8]=1.O.[OH-].[Na+]>O1CCCC1>[Br:6][C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH3:18])[C:10]2[CH:23]=[CH:24][CH:25]=[CH:26][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21505301HCID 21505301, compound

Product 1

HCID 21505296HCID 21505296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 275 parts of a 3 1/2% solution of lithium aluminate(1-) in tetrahydrofuran at 0°-5° is slowly added, with vigorous stirring, 15 parts of concentrated sulfuric acid. The resultant mixture is stirred at 0°-5° for 1 hour, whereupon a solution of 34 parts of ethyl 10-bromo-5H-dibenz[b,f]azepine-5-carboxylate in 225 parts of tetrahydrofuran is introduced. The mixture thus obtained is stirred for 1 hour, whereupon a solution of 20 parts of water in 40 parts of tetrahydrofuran, followed by 30 parts of aqueous 25% sodium hydroxide and then finally by 30 parts of water, is added. Insoluble solids are filtered out and washed with several portions of tetrahydrofuran. Washings and filtrate are combined, dried over magnesium sulfate, and stripped of solvent by vacuum distillation to give 10-bromo-5-methyl-5H-dibenz[b,f]azepine as the residue.

Workup

  1. additionis introduced
  2. customThe mixture thus obtained
  3. filtrationInsoluble solids are filtered out
  4. washwashed with several portions of tetrahydrofuran
  5. dry with materialdried over magnesium sulfate
  6. distillationstripped of solvent by vacuum distillation

Sources & evidence

ORD record
ord-efe8c9db06804fbdaf4610de706eb03f
Source dataset
uspto-grants-1976_10
Patent number
US03985730

Reaction notes

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