Phosgene → HCID 20450024, compound

HRID 358061Notes

Reaction equation

HRID 358061 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.[C:22](Cl)(Cl)=[O:23]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:22](=[O:23])[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

5

Reactant 2

HCID 6371PhosgeneHCID 20449973HCID 20449973, compound

Product 1

HCID 20450024HCID 20450024, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

0.15 g of 7-chloro-5-(2-fluorophenyl)-2-hydrazino-3H-1-benzazepine is dissolved in 10 ml of pyridine and treated with 1.44 ml of a 14.3% solution of phosgene in toluene. The mixture is heated to 60° for 5 minutes and then evaporated in vacuo. The residue is partitioned between benzene and water. The benzene phase is washed successively with water, with sodium hydrogen carbonate solution and with water. The solvent is evaporated in vacuo. The residue is chromatographed on 15 g of silica gel while eluting with benzene/ethyl acetate (19:1 and 9:1). After recrystallization from ether/hexane, there is obtained pure 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. temperatureThe mixture is heated to 60° for 5 minutes
  2. customevaporated in vacuo
  3. customThe residue is partitioned between benzene and water
  4. washThe benzene phase is washed successively with water, with sodium hydrogen carbonate solution and with water
  5. customThe solvent is evaporated in vacuo
  6. customThe residue is chromatographed on 15 g of silica gel
  7. washwhile eluting with benzene/ethyl acetate (19:1 and 9:1)
  8. customAfter recrystallization from ether/hexane

Sources & evidence

ORD record
ord-6b4689f3149c44fa96782260fb471bcb
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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