Methyl 2-chloroacrylate → HCID 13115071, compound

HRID 2272860Notes

Reaction equation

HRID 2272860 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 carboxylic acid obtained in Step A (63.6 mmol) in 65 mL of dichloroethane there are added in succession 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 1.5 hours. It is then brought to ambient temperature, and then 5 mL of methyl 2-chloroacrylate (48.9 mmol) and, dropwise, 9 mL of N,N,N-triethylamine (64 mmol) are added. The whole is heated at reflux overnight.

Workup

  1. temperatureThe reaction mixture is then refluxed for 1.5 hours
  2. customis then brought to ambient temperature
  3. temperatureThe whole is heated
  4. temperatureat reflux overnight

Sources & evidence

ORD record
ord-1fe896db5ca243798f8ad486a2efb636
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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