Acetic Acid → 8-chloro-2,3-dihydro-6-phenyl-11H-imidazo(2,1-b) (1,3,4)benzotriazepine

HRID 839267Notes

Reaction equation

HRID 839267 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([C:6](=S)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:5].C(O)(=O)C>C(Cl)Cl>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[NH:7][C:6]3=[N:1][CH2:2][CH2:3][N:4]3[N:5]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 20346884HCID 20346884, compound

Product 1

HCID 1355740718-chloro-2,3-dihydro-6-phenyl-11H-imidazo(2,1-b) (1,3,4)benzotriazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing 10.0 grams of the intermediate 1-(2-aminoethyl)-N-(2-benzoyl-4-chlorophenyl)-hydrazinecarbothioamide (Example 14) and 200 ml of glacial acetic acid was refluxed for 30 minutes with stirring. The acetic acid was removed in vacuo to leave a yellow oil. The residue was dissolved in methylenechloride, washed with separate rinses of 10% sodium hydroxide and water, and dried with magnesium sulfate. The solvent was evaporated to leave the 8-chloro-2,3-dihydro-6-phenyl-11H-imidazo(2,1-b)(1,3,4)benzotriazepine. The product was recrystallized from isopropanol to yield yellow crystals having a melting point of 191.5° to 193.5° C. Infrared analysis was used to confirm the structure.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customThe acetic acid was removed in vacuo
  3. customto leave a yellow oil
  4. washwashed with separate rinses of 10% sodium hydroxide and water
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-61536c5e1e054eb5af0064b4ca909f5f
Source dataset
uspto-grants-1978_06
Patent number
US04094871

Reaction notes

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