Methyl Acrylate → HCID 69893516, compound

HRID 2417532Notes

Reaction equation

HRID 2417532 reaction equation
Br[C:2]1[C:7]([CH2:8][NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N(CC)CC)C.[C:36]([O:40][CH3:41])(=[O:39])[CH:37]=[CH2:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([CH:8]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:7]2[C:6]([N+:16]([O-:18])=[O:17])=[CH:5][CH:4]=[CH:3][C:2]=2[CH:38]=[CH:37][C:36]([O:40][CH3:41])=[O:39])=[O:25])=[CH:22][CH:21]=1

Participants

10

Reactant 5

HCID 7294Methyl AcrylateHCID 8471Triethylamine2×HCID 85014-Chlorobenzoyl chlorideHCID 11776TriphenylphosphineHCID 85877337HCID 85877337, compound

Product 1

HCID 69893516HCID 69893516, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5.1 g (16.8 mmol) of ethyl (6-bromo-2-nitrobenzyl)aminoacetate was dissolved in 100 ml of dichloromethane. 2.4 ml (19.3 mmol) of 4-chlorobenzoyl chloride and 3.6 ml (25.2 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the crude product was obtained. The crude product was dissolved in 50 ml of DMF. 171 mg (0.75 mmol) of palladium acetate, 2.1 ml (22 mmol) of methyl acrylate, 292 mg (1.5 mmol) of triphenylphosphine and 3.0 ml (9.24 mmol) of triethylamine were added to the obtained solution and they were stirred at 100° C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the crude product was obtained. The crude product was then purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice for 2 hours
  3. stirringwere stirred at 100° C. overnight
  4. customThe crude product was then purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-4c12f28c3c944732bf07db3dc47e92aa
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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