Methyl Acrylate → N-Methyl-N-(4-methoxybenzyl)-4-(2-(methoxycarbonyl)ethenyl)phenylsulfonamid
Reaction equation
[CH3:1][N:2]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[S:3]([C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[C:29]([O:33][CH3:34])(=[O:32])[CH:30]=[CH2:31]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[CH3:1][N:2]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:31]=[CH:30][C:29]([O:33][CH3:34])=[O:32])=[CH:8][CH:7]=1)(=[O:5])=[O:4]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
A mixture of N-methyl-N-(4-methoxybenzyl)-4-bromophenylsulfonamide (1.68 g, 4.54 mmol), Pd(OAc)2 (20 mg, 0.091 mmol), tri-o-tolylphosphine (55 mg, 0.18 mmol), triethylamine (1.25 mL), acetonitrile (2.5 mL) and methyl acrylate (0.83 mL, 9.08 mmol) were placed in a stainless steel bomb and heated to about 120° C. for 4 hours. The mixture was cooled to 0° C., the bomb was vented, and the solid reaction mixture was collected, washed with ether and dried to afford 2.1 g of crude product which was used directly in the next step without further purification.
Workup
- temperatureThe mixture was cooled to 0° C.
- customthe solid reaction mixture
- customwas collected
- washwashed with ether
- customdried
Sources & evidence
- ORD record
- ord-6a0d4102900f4010bdfd66f349000f77
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380721
Reaction notes
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