Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-Methoxyethanol | HCID 8019 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Benzene, 1-(chloromethyl)-3(or 4)-ethenyl- | HCID 11768772 | — |
| Reactant | Sodium 2-(methylamino)ethanesulfonate | HCID 23684896 | — |
| Catalyst | 4-Nitrosophenol | HCID 7729 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 53949883 | HCID 53949883 | 70.6% |
Reaction Steps
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:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04309327 |
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| Source dataset | uspto-grants-1982_01 |
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| ORD ID | ord-9ff6caebbaaf4fde89a70b8b5b49f717 |
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| Source note | uspto-grants-1982_01 |
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