Methyl 2-chloroacrylate → HCID 13115071, compound

HRID 518912Notes

Reaction equation

HRID 518912 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1C(O)=O)=O.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.Cl[C:24](=[CH2:29])[C:25]([O:27][CH3:28])=[O:26].C(N(CC)CC)C>ClC(Cl)C>[C:24]1([C:25]([O:27][CH3:28])=[O:26])[CH:29]=[CH:1][N:3]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH2:8]2

Participants

6

Reactant 4

HCID 6659Methyl 2-chloroacrylate2×HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 574442HCID 574442, compound

Product 1

HCID 13115071HCID 13115071, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 10 g of the carboxylic acid obtained in Step A (63.6 mmol) in 65 mL of dichloroethane there are successively added 13.4 g of tosyl chloride (70.4 mmol), 11.5 mL of methyl 2-chloroacrylate (113.5 mmol) and then, dropwise, 17.8 mL of N,N,N-triethylamine (127.2 mmol). The reaction mixture is then refluxed for 1 hour 30 minutes. It is then placed at ambient temperature, and there are then added 5 mL of methyl 2-chloroacrylate (48.9 mmol) and, dropwise, 9 mL of N,N,N-triethylamine (64 mmol). The batch is refluxed overnight.

Workup

  1. temperatureThe reaction mixture is then refluxed for 1 hour 30 minutes
  2. customis then placed at ambient temperature
  3. temperatureThe batch is refluxed overnight

Sources & evidence

ORD record
ord-8c7139ad56694566aa099e7039098279
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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