Methyl 2-chloroacrylate → HCID 59437102, compound

HRID 2272865Notes

Reaction equation

HRID 2272865 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]=O)[CH:10](C([O-])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].S(Cl)(C1C=CC(C)=CC=1)(=O)=O.Cl[C:32](=[CH2:37])[C:33]([O:35][CH3:36])=[O:34].C(N(CC)CC)C>ClC(Cl)C.C(OCC)(=O)C>[CH2:9]1[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][CH2:12][N:11]2[CH:14]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:10]12

Participants

7

Reactant 4

HCID 6659Methyl 2-chloroacrylateHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 117874295HCID 117874295, compound

Product 1

HCID 59437102HCID 59437102, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 29 g of the compound obtained in Step B (103 mmoles) in 800 mL of dichloroethane there are added in succession 24 g of tosyl chloride (124 mmol), 12.6 mL of methyl 2-chloroacrylate (124 mmol) and then 35 mL of triethylamine (247 mmoles). The whole is stirred at reflux for 2 hours. After cooling, the reaction mixture is diluted with ethyl acetate, and the organic phase is washed with a saturated NaCl solution until neutral. After drying over MgSO4, filtration and concentration to dryness, the title product is isolated by chromatography over silica gel (petroleum ether/AcOEt gradient: 0-20%) in the form of a solid.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureAfter cooling
  3. washthe organic phase is washed with a saturated NaCl solution until neutral
  4. dry with materialAfter drying over MgSO4, filtration and concentration to dryness

Sources & evidence

ORD record
ord-7cb96e5d7b8d454e9f7bfddfeb624b34
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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