Hydrochloric Acid → HCID 20438182, compound

HRID 1979682Notes

Reaction equation

HRID 1979682 reaction equation
[NH2:1][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].Cl>C(#N)C.C(OC)(OC)(OC)CCC>[CH3:11][N:10]1[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:7]1[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13376543HCID 13376543, compound

Product 1

HCID 20438182HCID 20438182, compoundYield 192.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 1235121,1,1-TrimethoxybutaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2.37 g (0.01 m) of 1-[(2-aminophenyl)methyl]-2-methyl-1-phenylhydrazine of Example 9c in 40 ml of acetonitrile and 2.96 g (0.02 m) of trimethyl orthobutyrate, enough ethereal HCl was added to make the solution acidic. The mixture was warmed at 50° C. for 2.5 hours and then refluxed for 3.5 hours. The solvent was evaporated and the residue partitioned between 10% NaOH and ether. The ether solution was extracted with 5% HCl. The aqueous acidic solution was basified with 10% NaOH and the product was extracted with ether. The ether extract was dried (Na2SO4), filtered and evaporated to give 2.8 g (93%) of 4,5-dihydro-3-methyl-4-phenyl-2-n-propyl-3H-1,3,4-benzotriazepine as an oil.

Workup

  1. temperaturerefluxed for 3.5 hours
  2. customThe solvent was evaporated
  3. customthe residue partitioned between 10% NaOH and ether
  4. extractionThe ether solution was extracted with 5% HCl
  5. extractionthe product was extracted with ether
  6. extractionThe ether extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-92a6af00c47246adab740ee39b168689
Source dataset
uspto-grants-1984_11
Patent number
US04482547

Reaction notes

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