Ethanolamine → HCID 21388671, compound

HRID 1833290Notes

Reaction equation

HRID 1833290 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[OH-].[K+].[NH2:7][C:8]1[C:13]([Cl:14])=[CH:12][N:11]=[C:10](Cl)[C:9]=1[Cl:16]>CS(C)=O>[NH2:7][C:8]1[C:13]([Cl:14])=[CH:12][N:11]=[C:10]([O:4][CH2:3][CH2:2][NH2:1])[C:9]=1[Cl:16]

Participants

5

Reactant 3

HCID 700Ethanolamine2×HCID 14797Potassium Hydroxide3×HCID 7286762,3,5-trichloropyridin-4-amine

Product 1

HCID 21388671HCID 21388671, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
150 °C

Procedure

A mixture containing 21.4 grams (0.35 mole) of 2-aminoethanol, 50 milliliters of dimethylsulfoxide and 20 grams (0.36 mole) of potassium hydroxide was heated at 110° C. until all of the potassium hydroxide was reacted. The solution was added to a mixture containing 69 grams (0.35 mole) of 4-amino-2,3,5-trichloropyridine dissolved in 200 milliliters of dimethylsulfoxide. The mixture was heated for 11/2 hours at 138° C. to 150° C. under agitation and thereafter quenched by pouring into ice water. The solid which precipitated was recovered by filtration under reduced pressure, dried and recrystallized from a mixture of hexane and chloroform. The solid was dissolved in 100 milliliters of dimethylsulfoxide and mixed with a solution composed of 21.4 grams (0.35 mole) of 2-aminoethanol and 20 grams (0.36 mole) of potassium hydroxide dissolved in 50 milliliters of dimethylsulfoxide. This mixture was heated for 2 hours at 150° C., cooled by quenching with ice water to precipitate the product as a solid which was recovered by filtration under reduced pressure. This product was distilled under azeotropic conditions with benzene to remove water from the 4-amino-2-(2-aminoethoxy)-3,5-dichloropyridine product which has a melting point of 115°-116.5° C.

Workup

  1. customwas reacted
  2. additionThe solution was added to a mixture
  3. temperatureThe mixture was heated for 11/2 hours at 138° C. to 150° C. under agitation
  4. customquenched
  5. additionby pouring into ice water
  6. customThe solid which precipitated
  7. filtrationwas recovered by filtration under reduced pressure
  8. customdried
  9. customrecrystallized from a mixture of hexane and chloroform
  10. dissolutionThe solid was dissolved in 100 milliliters of dimethylsulfoxide
  11. additionmixed with a solution
  12. temperaturecooled
  13. customby quenching with ice water
  14. customto precipitate the product as a solid which
  15. filtrationwas recovered by filtration under reduced pressure
  16. distillationThis product was distilled under azeotropic conditions with benzene
  17. customto remove water from the 4-amino-2-(2-aminoethoxy)-3,5-dichloropyridine product which

Sources & evidence

ORD record
ord-6158d2b25e024c3dab2342bf1e0a3b58
Source dataset
uspto-grants-1978_01
Patent number
US04066438

Reaction notes

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