Chloroacetyl chloride → HCID 20449978, compound

HRID 358064Notes

Reaction equation

HRID 358064 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.[Cl:22][CH2:23][C:24](Cl)=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:24]([CH2:23][Cl:22])=[N: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

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 20449973HCID 20449973, compound

Product 1

HCID 20449978HCID 20449978, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 18.2 g of 7-chloro-5-(2-fluorophenyl)-2-hydrazino-3H-1-benzazepine in 220 ml of glacial acetic acid is treated dropwise at 15° with 5.1 ml of chloroacetyl chloride. The mixture is stirred at room temperature for a further 2 hours. The mixture is treated with 7.5 g of sodium acetate, stirred at room temperature for 2 hours. and at boiling under reflux for 20 minutes, then evaporated in vacuo and the residue is partitioned between chloroform and water. The organic phase is washed with sodium hydrogen carbonate solution and water and evaporated. The crude product obtained is chromatographed on silica gel while eluting with chloroform/ethanol (98.5:1.5) and there is obtained 8-chloro-1-(chloromethyl)-6-(2-fluorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine as white crystals of melting point 180° (decomposition).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. temperatureunder reflux for 20 minutes
  3. customevaporated in vacuo
  4. customthe residue is partitioned between chloroform and water
  5. washThe organic phase is washed with sodium hydrogen carbonate solution and water
  6. customevaporated
  7. customThe crude product obtained
  8. customis chromatographed on silica gel
  9. washwhile eluting with chloroform/ethanol (98.5:1.5)

Sources & evidence

ORD record
ord-3290f43c4ab74b93842bdd3e4b645d7a
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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