Ethylenediamine → 3-(benzyloxy)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxyaniline

HRID 1259497Notes

Reaction equation

HRID 1259497 reaction equation
[NH2:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[S].[CH2:21](N)[CH2:22][NH2:23]>>[CH2:13]([O:12][C:8]1[C:9]([O:10][CH3:11])=[C:2]([C:3]([C:4]2[NH:23][CH2:22][CH2:21][N:5]=2)=[CH:6][CH:7]=1)[NH2:1])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 582198492-Amino-4-(benzyloxy)-3-methoxybenzonitrile

Product 1

HCID 70592683-(benzyloxy)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxyaniline

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-4-(benzyloxy)-3-methoxybenzonitrile (144 g, 566 mmol) and sulfur (55 g, 1.7 mol) in ethylenediamine (800 mL) was degassed for 30 minutes then heated to 100° C. After 16 h the reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated under reduced pressure, diluted with a saturated sodium bicarbonate solution and extracted with EtOAc. The organic layer was washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure.

Workup

  1. customwas degassed for 30 minutes
  2. temperatureAfter 16 h the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additiondiluted with a saturated sodium bicarbonate solution
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0cf5377aa224aedb286ce5b51ed957c
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

Loading…