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

HRID 1448413ノート

反応式

HRID 1448413 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c528de26dbd14cfb90d65708371046f3
出典データセット
uspto-grants-1979_12
特許番号
US04180395

反応ノート

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