1,3-Diazepan-2-one hydrazone hydroiodide → 1,5-Bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-one-4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ylhydrazone

HRID 1701138Notes

Reaction equation

HRID 1701138 reaction equation
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12](=O)[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.I.[NH:30]1[CH2:36][CH2:35][CH2:34][CH2:33][N:32]=[C:31]1[NH:37][NH2:38]>C(O)(C)C>[NH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][N:30]=[C:31]1[NH:37][N:38]=[C:12]([CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH:11]=[CH:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][C:2]([F:28])([F:27])[F:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 131940841,3-Diazepan-2-one hydrazone hydroiodideHCID 543760901,5-Bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-one

Product 1

HCID 570149011,5-Bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-one-4,5,6,7-tetrahydro-1H-1,3-diazepin-2-ylhydrazoneYield 75%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-15 °C

Procedure

A mixture of 1,5-bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-one (4.0 g; 0.01 mole), 4,5,6,7-tetrahydro-1H-1,3-diazepine-2-ylhydrazine hydroiodide (2.6 g; 0.01 mole) and isopropyl alcohol (25 ml) is heated at reflux for 2 to 3 hours. The reaction mixture is then cooled to -15° C., and the precipitated material is isolated by filtration and washed with ether. The isolated material is mixed with ether and saturated sodium carbonate solution and the mixture stirred for about 15 minutes. The ether layer is then separated, dried, and concentrated to afford 3.8 g (75%) of title product, a bright yellow solid, m.p. 184.5°-185.5° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 to 3 hours
  3. customthe precipitated material is isolated by filtration
  4. washwashed with ether
  5. additionThe isolated material is mixed with ether and saturated sodium carbonate solution
  6. customThe ether layer is then separated
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6ceef21f65b04064991a3d0891078ccb
Source dataset
uspto-grants-1980_03
Patent number
US04191768

Reaction notes

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