Benzylamine → HCID 20277893, compound

HRID 1248431Notes

Reaction equation

HRID 1248431 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][CH2:7]OS(C)(=O)=O)(=[O:4])=[O:3].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OC(=O)C)C>[CH2:13]([NH:20][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 20277903HCID 20277903, compound

Product 1

HCID 20277893HCID 20277893, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Methanesulphonamido 2-methanesulphonyloxyethane (23.3 g) was added in small portions to benzylamine (24 ml) at such a rate that the temperature did not rise above 30° C. When the addition was complete the mixture was stirred at room temperature for one hour. Ethylacetate (150 ml) was then added to the mixture and the precipitated solid was filtered off. The filtrate was evaporated and the product isolated by column chromatography of the residue using gradient elution (Kieselgel, ethylacetate going to 30% methanol in ethylacetate as eluent). The product was recrystallised from ethylacetate-petroleum ether to give 10.9 g of pale yellow crystals, mpt 71°-73° C.

Workup

  1. customdid not rise above 30° C
  2. additionWhen the addition
  3. filtrationthe precipitated solid was filtered off
  4. customThe filtrate was evaporated
  5. customthe product isolated by column chromatography of the residue
  6. washelution (Kieselgel, ethylacetate going to 30% methanol in ethylacetate as eluent)
  7. customThe product was recrystallised from ethylacetate-petroleum ether

Sources & evidence

ORD record
ord-f7bce85a600c4e09b98017d102ddd1bf
Source dataset
uspto-grants-1985_06
Patent number
US04524073

Reaction notes

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