Glycine → HCID 13958730, compound

HRID 255941Notes

Reaction equation

HRID 255941 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[Cl:6][C:7]1[C:17]([Cl:18])=[C:16]([C:19](=[O:24])[C:20](=[CH2:23])[CH2:21][CH3:22])[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11](Cl)=[O:12]>O1CCCC1>[Cl:6][C:7]1[C:17]([Cl:18])=[C:16]([C:19](=[O:24])[C:20](=[CH2:23])[CH2:21][CH3:22])[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:12]

Participants

4

Reactant 2

HCID 750GlycineHCID 13958729HCID 13958729, compound

Product 1

HCID 13958730HCID 13958730, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring suspension of finely ground glycine (6.01 g, 0.08 mole) in tetrahydrofuran (50 ml) was added, dropwise, the solution of [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]acetyl chloride over a period of 15 minutes. The mixture was stirred at ambient temperature for 2.25 hours and then at reflux for one hour. The mixture was cooled, filtered and washed with tetrahydrofuran. The solid was suspended in water (60 ml), filtered, washed with water and dried to give 7.15 g of N-{[2,3-dichloro-4(2-methylenebutyryl)phenoxy]acetyl}glycine. Upon recrystallization from isopropyl alcohol, the product melted at 201.5°-202.5° C.

Workup

  1. additionwas added
  2. temperatureat reflux for one hour
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washwashed with tetrahydrofuran
  6. filtrationfiltered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-cf2d49ee54e440d384efc26cc6afec18
Source dataset
uspto-grants-1987_10
Patent number
US04699926

Reaction notes

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