Water → HCID 21388672, compound

HRID 1833292Notes

Reaction equation

HRID 1833292 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([O:9][CH2:10][CH2:11][OH:12])[C:3]=1[Cl:13].[C:14](Cl)(=[O:16])[CH3:15].O>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([O:9][CH2:10][CH2:11][O:12][C:14](=[O:16])[CH3:15])[C:3]=1[Cl:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 213886662-[(4-Amino-3,5-dichloropyridin-2-yl)oxy]ethan-1-ol

Product 1

HCID 21388672HCID 21388672, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 22.3 grams (0.1 mole) of 4-amino-3,5-dichloro-2-(2-hydroxyethoxy)pyridine (prepared by the method of Example I) dissolved in 150 milliliters of pyridine was added dropwise, with agitation, 8.7 grams (0.11 mole) of acetylchloride. The mixture was brought to reflux (~100° C.) and held at this temperature for 1 hour. The mixture was cooled to room temperature and poured into water. The oil which separated was extracted with methylene chloride, washed with 200 milliliters of water and dried over potassium carbonate. The solvent was evaporated under reduced pressure and the 4-amino-3,5-dichloro-2-(2-acetoxyethoxy)pyridine product was recovered by recrystallization from hexane. The product was recovered in a yield of 13.7 grams which melts at 76°-77° C.

Workup

  1. temperatureto reflux (~100° C.)
  2. customThe oil which separated
  3. extractionwas extracted with methylene chloride
  4. washwashed with 200 milliliters of water
  5. dry with materialdried over potassium carbonate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe 4-amino-3,5-dichloro-2-(2-acetoxyethoxy)pyridine product was recovered by recrystallization from hexane
  8. customThe product was recovered in a yield of 13.7 grams which melts at 76°-77° C.

Sources & evidence

ORD record
ord-e286ef2f13094fe8abb3a3b2fa26f6eb
Source dataset
uspto-grants-1978_01
Patent number
US04066438

Reaction notes

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