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Hydrochloric Acid → HCID 86739543, compound

HRID 1980341
Notes
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Reaction equation

HRID 1980341 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13751050VinylbenzylamineHCID 21958458HCID 21958458, compound

Product 1

HCID 86739543HCID 86739543, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 785
Hydroquinone
Catalyst
HCID 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 of 36.1 g of β-chloroethylsulfonylpropionic acid chloride 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 1,500 ml of ice water, and a precipitate was filtered off. The precipitate was recrystallized from a mixed solvent of 200 ml of ethanol and 200 ml of water to provide 26.8 g of N-vinylbenzyl-β-chloroethylsulfonyl propionic acid amide. Yield was 57%.

Workup

  1. customwas placed in a reactor
  2. waitto stand overnight at room temperature
  3. additionThe reaction mixture was then poured into a solution
  4. customprepared
  5. filtrationa precipitate was filtered off
  6. customThe precipitate was recrystallized from a mixed solvent of 200 ml of ethanol and 200 ml of water

Sources & evidence

ORD record
ord-b6e762eba5324d1c95ec6905f0b1a84f
Source dataset
uspto-grants-1985_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04508818

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes