Ethanol → HCID 12813978, compound

HRID 1579151Notes

Reaction equation

HRID 1579151 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH3:16])[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[CH2:19](O)[CH3:20].C([O-])([O-])OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH3:16])[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[C:10]([O:11][CH2:19][CH3:20])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 12813977HCID 12813977, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 12813978HCID 12813978, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 29.5 g of 2-bromo-5-methyl-10,11-dihydro [5H] dibenzo (b,f) azepine-11-one, 295 ml of ethanol and 29.5 ml of ethyl orthoformate was heated to 70°C and then 1 g of p-toluene sulfonic acid was added thereto in small fractions. The mixture was held at 70°C for 11/2 hours and then 15 ml of triethylamine were added dropwise while still hot and the mixture was then cooled. The product crystallized and the mixture was diluted with 300 ml of distilled water, was stirred at room temperature for 30 minutes and was vacuum filtered. The recovered precipitate was washed with water and dried to obtain 31.8 g of 2-bromo-5-methyl-11-ethoxy [5H] dibenzo (b,f) azepine as pale yellow crystals melting at 131°C.

Workup

  1. customwas held at 70°C for 11
  2. custom2 hours
  3. temperaturewas then cooled
  4. customThe product crystallized
  5. additionthe mixture was diluted with 300 ml of distilled water
  6. filtrationfiltered
  7. washThe recovered precipitate was washed with water
  8. customdried

Sources & evidence

ORD record
ord-44add63850ee4197938eddbf20874eb0
Source dataset
uspto-grants-1976_01
Patent number
US03931151

Reaction notes

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