Glycine → N-[(3,5-Dichloro-6-fluoro-2-pyridyloxy)-acetyl]glycine

HRID 1448413Notes

Reaction equation

HRID 1448413 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[Cl:8][C:9]1[C:10]([O:17][CH2:18][C:19](Cl)=[O:20])=[N:11][C:12]([F:16])=[C:13]([Cl:15])[CH:14]=1>O.C1C=CC=CC=1>[Cl:8][C:9]1[C:10]([O:17][CH2:18][C:19]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:20])=[N:11][C:12]([F:16])=[C:13]([Cl:15])[CH:14]=1

Participants

6

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 20379628(3,5-Dichloro-6-fluoro-2-pyridyloxy)acetyl chloride

Product 1

HCID 20379606N-[(3,5-Dichloro-6-fluoro-2-pyridyloxy)-acetyl]glycine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A solution was prepared by admixing 2.93 grams (0.039 mole) of glycine with 4.67 grams (0.117 mole) of sodium hydroxide in 117 milliliters of water. To this solution was added 10.0 grams of (3,5-dichloro-6-fluoro-2-pyridyloxy)acetyl chloride in 30 milliliters of benzene. The mixture was allowed to stand at a temperature of ~2°-5° C. for about 10 minutes and the mixture was warmed to room temperature and stirred for about 30 minutes. The reaction mixture was diluted with additional benzene and the aqueous layer which formed was removed and acidified. The solid which precipated was removed by filtration, dried and recrystallized from 50 percent ethanol. The N-[(3,5-dichloro-6-fluoro-2-pyridyloxy)acetyl]glycine product was recovered in a yield of 5.0 grams and melted at 155°-157° C. and upon analysis was found to have carbon, hydrogen, chlorine and nitrogen contents of 35.7, 2.1, 24.2 and 8.7 percent, respectively as compared with the theoretical contents of 36.5, 2.4, 23.9 and 9.4 percent, respectively, calculated for the above named compound.

Workup

  1. customA solution was prepared
  2. customthe aqueous layer which formed
  3. customwas removed
  4. customThe solid which precipated was removed by filtration
  5. customdried
  6. customrecrystallized from 50 percent ethanol
  7. customThe N-[(3,5-dichloro-6-fluoro-2-pyridyloxy)acetyl]glycine product was recovered in a yield of 5.0 grams and melted at 155°-157° C. and upon analysis

Sources & evidence

ORD record
ord-c528de26dbd14cfb90d65708371046f3
Source dataset
uspto-grants-1979_12
Patent number
US04180395

Reaction notes

Loading…