8-Chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione → HCID 178477862, compound

HRID 580861Notes

Reaction equation

HRID 580861 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8](=S)[NH:7][C:6]=2[CH:17]=1.[NH2:18][CH2:19][CH2:20][C:21]1[N:25]=[CH:24][NH:23][CH:22]=1>C(OCCO)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([NH:18][CH2:19][CH2:20][C:21]3[NH:25][CH:24]=[N:23][CH:22]=3)=[N:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 125357788-Chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thioneHCID 178419017HCID 178419017, compound

Product 1

HCID 178477862HCID 178477862, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 5.8 g (0.022 mol) of 8-chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione in 145 mL of 2-ethoxyethanol was treated with 4.94 g (0.044 mol) of histamine and heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed three times with H2O, then saturated NaHCO3 solution, then saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product as a yellow foam. This was dissolved in CH2Cl2 and slowly treated with hexane to give 7.44 g (99.2% yield) of the product as an amorphous yellow solid. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =338.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washwashed three times with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product as a yellow foam
  7. dissolutionThis was dissolved in CH2Cl2
  8. additionslowly treated with hexane

Sources & evidence

ORD record
ord-018d07cba3684381ae42da535fcfaf9c
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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