1-Butanol → HCID 20449965, compound

HRID 358055Notes

Reaction equation

HRID 358055 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.[CH2:22](O)CCC>C(OCC)(OCC)OCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH: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

4

Reactant 2

HCID 2631-ButanolHCID 20449973HCID 20449973, compound

Product 1

HCID 20449965HCID 20449965, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

12.1 g of 7-chloro-5-(2-fluorophenyl)-2-hydrazino-3H-1-benzazepine are heated to boiling under reflux for 2 hours in a mixture of 330 ml of n-butanol and 110 ml of triethyl orthoformate. The mixture is evaporated in vacuo. The residue is crystallized from hexane, there being obtained crude 8-chloro-6-(2-fluorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine as reddish coloured crystals. This material is purified by chromatography on 121 g of silica gel. Impurities are eluted with benzene/methanol (99:1). The product is subsequently eluted with benzene/methanol (98.5:1.5 and 98:2). After crystallization of the resulting material from ether, there is obtained 8-chloro-6-(2-fluorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine of melting point 180°-182°.

Workup

  1. customThe mixture is evaporated in vacuo
  2. customThe residue is crystallized from hexane, there
  3. custombeing obtained crude 8-chloro-6-(2-fluorophenyl)-4H-s-triazolo[4,3-a][1]benzazepine as reddish coloured crystals
  4. customThis material is purified by chromatography on 121 g of silica gel
  5. washImpurities are eluted with benzene/methanol (99:1)
  6. washThe product is subsequently eluted with benzene/methanol (98.5:1.5 and 98:2)
  7. customAfter crystallization of the resulting material from ether

Sources & evidence

ORD record
ord-1719aacf80fe4b31aac6e9d8425e6285
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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