Hydrochloric Acid → HCID 13376557, compound

HRID 1979681Notes

Reaction equation

HRID 1979681 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:10][CH3:11].C(OCC)(OCC)(OCC)C.[ClH:29].[C:30](#[N:32])[CH3:31]>>[ClH:29].[CH3:31][C:30]1[N:10]([CH3:11])[N:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:8][C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=2[N:32]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 66221Triethyl orthoacetateHCID 13376543HCID 13376543, compound

Product 1

HCID 13376557HCID 13376557, compoundYield 60%

Procedure

To a solution of 3.5 g (0.0154 m) of 1-[(2-aminophenyl)methyl]-2-methyl-1-phenylhydrazine of Example 9c in 40 ml of acetonitrile and 4.87 g (0.03 m) of triethyl orthoacetate was added sufficient ethereal HCl to make the solution acidic. The mixture was refluxed 5.5 hours. The solvents were evaporated and the residue was partitioned between 10% NaOH and ether. The ether extract was washed with water, dried (Na2SO4) and filtered. The product was precipitated with ethereal HCl to afford 2.63 g (60%) of 4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3,4-benzotriazepine hydrochloride, m.p. 274°-277° C.

Workup

  1. temperatureThe mixture was refluxed 5.5 hours
  2. customThe solvents were evaporated
  3. customthe residue was partitioned between 10% NaOH and ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe product was precipitated with ethereal HCl

Sources & evidence

ORD record
ord-965dc505e0334f6c96e443e8c373d6d0
Source dataset
uspto-grants-1984_11
Patent number
US04482547

Reaction notes

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