Sodium Hydroxide → HCID 20449976, compound

HRID 358060Notes

Reaction equation

HRID 358060 reaction equation
Br[C:2]1[N:6]2[C:7]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:8]=3[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[CH:10][CH2:11][C:5]2=[N:4][N:3]=1.[OH-:24].[Na+]>P(=O)(O)(O)O>[Cl:23][C:20]1[CH:21]=[CH:22][C:7]2[N:6]3[C:2](=[O:24])[NH:3][N:4]=[C:5]3[CH2:11][CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:8]=2[CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20450014HCID 20450014, compound

Product 1

HCID 20449976HCID 20449976, compound

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

9 g of 1-bromo-8-chloro-6-(2-chlorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine are stirred at 140° for 22 hours in 263 ml of 85% phosphoric acid. The mixture is poured on to 1.5 kg of ice water and neutralized with 28% sodium hydroxide solution. The product is extracted with chloroform. The residue from the chloroform extracts is chromatographed on 300 g of silica gel. Impurities are separated by elution with chloroform. By elution with chloroform which contains 2% or 4% ethanol, crystallization of the resulting material from diethyl ether/diisopropyl ether and recrystallization from ethyl acetate there is obtained 8-chloro-6-(2-chlorophenyl)-2,4-dihydro-1H-s-triazolo[4,3-a][1]benzazepin-1-one of melting point 250°-251°.

Workup

  1. extractionThe product is extracted with chloroform
  2. customThe residue from the chloroform extracts is chromatographed on 300 g of silica gel
  3. customImpurities are separated by elution with chloroform
  4. washBy elution with chloroform which
  5. custom2% or 4% ethanol, crystallization of the resulting material
  6. customfrom diethyl ether/diisopropyl ether and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-bc1956dd2deb4c69adc195d3b0496133
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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