Dichloromethane → HCID 178420787, compound

HRID 580866Notes

Reaction equation

HRID 580866 reaction equation
[CH:1]1[C:11]2[C:10](=S)[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(Cl)Cl>C(OCCO)C>[CH:1]1[C:11]2[C:10]([NH:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 310183-PyridinemethanamineHCID 303289111H-Dibenzo(b,e)(1,4)diazepine-11-thione, 5,10-dihydro-

Product 1

HCID 178420787HCID 178420787, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.6 g (2.7 mmol) of 5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione [German Patent, DE-2,306,762, C.A. 79:126533a (1973)] in 10 mL 2-ethoxyethanol was treated with 0.6 mL (5.4 mmol) of 3-(aminomethyl)pyridine 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 and saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with CHCl3 /MeOH (95/5) gave the product. On adding CH2Cl2, the product crystallized. There was obtained 459 mg (58.1% yield) of the pure product as a yellow solid, mp 150-152° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =301.

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
  7. washChromatography on silica gel, eluting with CHCl3 /MeOH (95/5)
  8. customgave the product
  9. customthe product crystallized

Sources & evidence

ORD record
ord-9a6793cce26e4ed392527c1879f55009
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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