Ammonium Chloride → 2-Chloro-N-({2-[(prop-2-en-1-yl)oxy]-1,3-dioxolan-4-yl}methyl)acetamide

HRID 1995807Notes

Reaction equation

HRID 1995807 reaction equation
[OH:1][CH:2]([CH2:9][OH:10])[CH2:3][NH:4][C:5](=[O:8])[CH2:6][Cl:7].[CH2:11]([O:14][CH:15](OCC=C)OCC=C)[CH:12]=[CH2:13].[Cl-].[NH4+]>ClC(Cl)C>[CH2:11]([O:14][CH:15]1[O:1][CH:2]([CH2:3][NH:4][C:5](=[O:8])[CH2:6][Cl:7])[CH2:9][O:10]1)[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 855903-{Bis[(prop-2-en-1-yl)oxy]methoxy}prop-1-eneHCID 13233120HCID 13233120, compound

Product 1

HCID 132331212-Chloro-N-({2-[(prop-2-en-1-yl)oxy]-1,3-dioxolan-4-yl}methyl)acetamideYield 33.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Six and seven-tenths g (0.04 mole) of N-(2,3-dihydroxypropyl) chloroacetamide, 7.3 g (0.04 mole) of triallylorthoformate, 0.2 g of ammonium chloride, and 50 ml of dichloroethane were combined in a reaction flask and distilled to a head temperature of 82° C. The distillate was cooled to room temperature, stirred with potassium carbonate and filtered over Florisil. The filtrate was evaporated to yield 3.2 g of 2-allyloxy-4-(chloroacetylamino) methyl-1,3-dioxolane, a yellow oil. Structure was confirmed by NMR. nD30 =1.4888.

Workup

  1. customwere combined in a reaction flask
  2. distillationdistilled to a head temperature of 82° C
  3. filtrationfiltered over Florisil
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-52625630d2a14b259dbf643f6b680a31
Source dataset
uspto-grants-1983_09
Patent number
US04406686

Reaction notes

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