Hydrochloric Acid → HCID 86739543, compound

HRID 1462575Notes

Reaction equation

HRID 1462575 reaction equation
C(N[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=C.[CH2:11]([N:13](CC)CC)[CH3:12].[Cl:18][CH2:19][CH2:20][S:21]([CH:24]([CH3:28])[C:25](Cl)=[O:26])(=[O:23])=[O:22].Cl>O1CCCC1.C1(C=CC(O)=CC=1)O>[CH:11]([NH:13][C:25](=[O:26])[C:24]([CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)([S:21]([CH2:20][CH2:19][Cl:18])(=[O:23])=[O:22])[CH3:28])=[CH2:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1375105010578-09-3HCID 21958458HCID 21958458, compound

Product 1

HCID 86739543HCID 86739543, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 100 ml of tetrahydrofuran, 20.1 g of vinylbenzylamine, 16.7 g of triethylamine, and 0.1 g of hydroquinone was placed in a reactor, and while cooling with ice water, a solution containing 36.1 g of β-chloroethylsulfonylpropionic acid chloride dissolved in 200 ml of tetrahydrofuran was added dropwise thereto over a period of 30 minutes. The resulting mixture was allowed to stand overnight at room temperature. The reaction mixture was then poured into a solution prepared by diluting 16.5 g of concentrated hydrochloric acid with 1.5 liters of ice water, and a precipitate was collected by filtration. The precipitate was recrystallized from a solvent mixture of 200 ml of ethanol and 200 ml of water to provide 26.8 g of N-vinylbenzyl-β-chloroethylsulfonyl propionic acid amide.

Workup

  1. customwas placed in a reactor
  2. additionwas added dropwise
  3. waitto stand overnight at room temperature
  4. additionThe reaction mixture was then poured into a solution
  5. customprepared
  6. filtrationa precipitate was collected by filtration
  7. customThe precipitate was recrystallized from a solvent mixture of 200 ml of ethanol and 200 ml of water

Sources & evidence

ORD record
ord-7498194b4a3e42d18a9561464830e7f7
Source dataset
uspto-grants-1984_07
Patent number
US04460680

Reaction notes

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