Water → HCID 20449987, compound

HRID 358070Notes

Reaction equation

HRID 358070 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH:10]([NH:12][NH2:13])[CH2:9][CH2:8][CH: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][CH2:8][CH: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 20449960HCID 20449960, compound

Product 1

HCID 20449987HCID 20449987, compound

Procedure

15.0 g of 7-chloro-5-(2-fluorophenyl)-2-hydrazino-4,5-dihydro-2H-1-benzazepine are dissolved in 200 ml of dimethylformamide. After adding 18 g of N,N'-carbonyl-diimidazole, the mixture is stirred at 52° for 20 hours, poured into 2 l of water and extracted with ethyl acetate. The organic extracts are washed with water, dried and evaporated. The residue is chromatographed on 800 g of silica gel. By elution with chloroform which contains 2% ethanol and crystallization from ether there is obtained 8-chloro-6-(2-fluorophenyl)-2,4,5,6-tetrahydro-1H-s-triazolo[4,3-a][1]benzazepin-1-one of melting point 236°-238°.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts are washed with water
  3. customdried
  4. customevaporated
  5. customThe residue is chromatographed on 800 g of silica gel
  6. washBy elution with chloroform which
  7. custom2% ethanol and crystallization from ether

Sources & evidence

ORD record
ord-66d5d456a1904b4280986144a7dbb0a7
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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