Methanol → HCID 4172278, compound

HRID 1390363Notes

Reaction equation

HRID 1390363 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH:7]=[NH:8])[CH3:3].[Cl:10][C:11]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:12]=1N.[CH3:21][OH:22]>>[CH3:21][O:22][C:7](=[N:8][C:12]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:11]=1[Cl:10])[CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 226912-Chloro-5-nitroanilineHCID 22749236HCID 22749236, compound

Product 1

HCID 4172278HCID 4172278, compound

Conditions

Temperature
20 °C

Procedure

To a flask equipped with stirrer and condenser are charged: 156.0 g (0.8 mole of ethyl-3-iminopropionate hydrochloride. 103.0 g (0.6 mole 2- chloro-5-nitroaniline, and 500 ml reagent grade methanol (anhydrous). The resulting mixture is stirred at room temperature (ca. 20° C.) for 20 hours, whereupon it is heated to reflux for one hour while being concentrated to a pot temperature of 100° C. while distilling off methanol at atmospheric pressure, cooled to room temperature, and ammonium chloride filtered off. The resulting salt is washed well with 200 ml of methanol (water free) and the filtrate cooled. The product is filtered to yield 84.6 g (47%), and recrystallized from isopropanol-heptane (50/50 by volume), to yield a product having a melting point of 60-62° C.

Workup

  1. customTo a flask equipped with stirrer and condenser
  2. additionare charged
  3. temperaturewhereupon it is heated
  4. temperatureto reflux for one hour
  5. concentrationwhile being concentrated to a pot temperature of 100° C.
  6. distillationwhile distilling off methanol at atmospheric pressure
  7. temperaturecooled to room temperature
  8. filtrationammonium chloride filtered off
  9. washThe resulting salt is washed well with 200 ml of methanol (water free)
  10. temperaturethe filtrate cooled
  11. filtrationThe product is filtered
  12. customto yield 84.6 g (47%)
  13. customrecrystallized from isopropanol-heptane (50/50 by volume)
  14. customto yield a product

Sources & evidence

ORD record
ord-8e2fd0cb1cf142f981fe0ae9d1bde2c5
Source dataset
uspto-grants-1979_02
Patent number
US04138571

Reaction notes

Loading…