Hydrochloric Acid → HCID 53949883, compound

HRID 1105496Notes

Reaction equation

HRID 1105496 reaction equation
[Na+].[CH3:2][NH:3][CH2:4][CH2:5][S:6]([O-:9])(=[O:8])=[O:7].C([CH:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=C.[OH-].[Na+].Cl.CO[CH2:25][CH2:26]O>N(C1C=CC(O)=CC=1)=O.O>[CH3:2][N:3]([CH:25]=[CH2:26])[CH:4]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][S:6]([OH:9])(=[O:8])=[O:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 80192-Methoxyethanol2×HCID 14798Sodium HydroxideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 23684896Sodium 2-(methylamino)ethanesulfonate

Product 1

HCID 53949883HCID 53949883, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 77294-NitrosophenolCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Into a 2 liter volume flask equipped with a stirrer, N-methyltaurine sodium salt (161 g), deionized water (400 g) and ethylene glycol monomethyl ether (300 g) were charged. The contents were maintained at 70° C. while stirring, and a mixture of vinylbenzyl chloride (153 g), ethylene glycol monomethyl ether (100 g) and p-nitrosophenol (0.15 g) was dropwise added thereto in 1 hour, during which sodium hydroxide (each 8 g) was added thereto 6 times with intervals of 10 minutes. Thereafter, stirring was continued for 5 hours. To the reaction mixture, conc. hydrochloric acid (120 g) was added, and the resulting mixture was concentrated in a rotary evaporator to make a 1/3 volume. The concentrate was admixed with a 4 time volume of acetone and filtered. The filtrate was concentrated to a 3/10 volume and admixed with acetone. The precipitated yellow solids were collected and recrystallized from deionized water to give N-methyl-N-vinylbenzyltaurine (180 g) of the formula:

Workup

  1. customInto a 2 liter volume flask equipped with a stirrer
  2. additionwas dropwise added
  3. customwith intervals of 10 minutes
  4. stirringThereafter, stirring
  5. waitwas continued for 5 hours
  6. concentrationthe resulting mixture was concentrated in a rotary evaporator
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated to a 3/10 volume
  9. customThe precipitated yellow solids were collected
  10. customrecrystallized from deionized water

Sources & evidence

ORD record
ord-9ff6caebbaaf4fde89a70b8b5b49f717
Source dataset
uspto-grants-1982_01
Patent number
US04309327

Reaction notes

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