Benzene → N-n-propyl-N-(1,3-dioxolan-2-ylmethyl)-alpha-chloroacetamide

HRID 1763768Notes

Reaction equation

HRID 1763768 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)[CH2:2][CH3:3].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>O>[CH2:1]([N:4]([CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)[C:25](=[O:26])[CH2:24][Cl:23])[CH2:2][CH3:3]

Participants

6

Procedure

N-n-Propyl-N-(1,3-dioxolan-2-ylmethyl)amine (10.5 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The mixture was cooled to about 5° to 10° C. and chloroacetyl chloride (5.5 ml) was added dropwise with stirring. After the addition was completed stirring was continued until the reaction mixture reached room temperature. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-n-propyl-N-(1,3-dioxolan-2-ylmethyl)-α-chloroacetamide as an oil.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture was cooled to about 5° to 10° C.
  4. additionAfter the addition
  5. stirringwas completed stirring
  6. customreached room temperature
  7. customAfter this time the organic phase was separated from the aqueous phase
  8. washwas washed with water
  9. dry with materialThe washed solution was then dried over anhydrous magnesium sulfate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-e9aac286747b43ce9ca07ef602c9f724
Source dataset
uspto-grants-1978_09
Patent number
US04113464

Reaction notes

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