Water → HCID 20450024, compound

HRID 358062Notes

Reaction equation

HRID 358062 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][CH:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1.O.CN(C)[CH:25]=[O:26]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:25](=[O:26])[NH:13][N:12]=[C:10]3[CH2:9][CH:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 20449973HCID 20449973, compound

Product 1

HCID 20450024HCID 20450024, compound

Procedure

3 g of 7-chloro-5-(2-fluorophenyl)-2-hydrazino-3H-1-benzazepine are dissolved in 40 ml of dimethylformamide. After adding 3.6 g of N,N'-carbonyldiimidazole, the mixture is stirred at 50° for 16 hours. The solution obtained is then poured into 700 ml of water and extracted with ethyl acetate. The organic extracts are washed with water and saturated sodium chloride solution, dried and evaporated. The residue is chromatographed on 200 g of silica gel while eluting with chloroform/ethanol (98.5:1.5). After recrystallization from diisopropyl ether, there is obtained 8-chloro-6-(2-fluorophenyl)-2,4-dihydro-1H-s-triazolo[4,3-a][1]benzazepin -1-one of melting point 223°-225°.

Workup

  1. customThe solution obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts are washed with water and saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on 200 g of silica gel
  7. washwhile eluting with chloroform/ethanol (98.5:1.5)
  8. customAfter recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-fe4a3aa1dde445c4941257ea677f8d7a
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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