تفاعل #642380
ord-7dea942669c84afbba076b0b7efa342e
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1workup.ADDITIONAfter complete addition (within 15 min)
- 2workup.STIRRINGis further stirred for 3 h at room temperature
- 3ترشيحThe obtained dark-brown mixture was filtered through a pad of 20 g of celite
- 4ترشيحfilter aid
- 5غسيلthe cake was washed with 60 ml of dichloromethane
- 6تركيزthe filtrate was concentrated to approximately ⅓,
- 7أخرىfollowed by precipitation with cyclohexane/hexane 50 ml/50 ml
- 8ترشيحThe obtained brown precipitate was filtered off
- 9غسيلwashed with 10 ml of hexane
- 10أخرىdried
الإجراء التجريبي
To an ice cooled solution of 1.47 g of 4-{[6-(acryloyloxy)hexyl]oxy}benzoic acid (5.00 mM) and 0.24 g of DMAP (2.00 mM) in 20 ml of dichloromethane, was added a solution of 1.03 g of DCC (5.00 mM) in 10 ml of dichloromethane dropwise. After complete addition (within 15 min) stirring was continued at 0° C. for further 90 min., then 2.57 g of 4-{6-[(E)-(4-{(E)-[4-(dimethylamino)phenyl]diazenyl}phenyl)-diazenyl]-2,3-dihydro-1H-perimidin-2-yl}-phenol (5.00 mM) were added to the reaction mixture which is further stirred for 3 h at room temperature. The obtained dark-brown mixture was filtered through a pad of 20 g of celite filter aid, the cake was washed with 60 ml of dichloromethane and the filtrate was concentrated to approximately ⅓, followed by precipitation with cyclohexane/hexane 50 ml/50 ml. The obtained brown precipitate was filtered off, washed with 10 ml of hexane and dried to give 3.80 g (4.80 mM, 96%) of 4-{6-[(E)-(4-{(E)-[4-(dimethylamino)phenyl]diazenyl}phenyl)diazenyl]-2,3-dihydro-1H-perimidin-2-yl}phenyl 4-{[6-(acryloyloxy)hexyl]oxy}benzoate dark-brown powder; λmax=547 nm, ε=53000 (THF). For total purification, the dye might be flash chromatographed on silica gel.