Hydrochloric Acid → HCID 3979718, compound

HRID 234570Notes

Reaction equation

HRID 234570 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[CH2:8]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl>O.O1CCOCC1>[CH2:8]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:19])=[CH:21][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium Hydroxide2×HCID 1708634-Hexylbenzoyl chloride

Product 1

HCID 3979718HCID 3979718, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

In a 200 ml-three-necked flask, 3.34 g (44.5 mM) of glycine, 0.89 g (22.3 mM) of sodium hydroxide and 16.7 ml of distilled water were placed and mixed. To the solution, 16.7 ml of dioxane was added. To the resultant mixture, a solution of 0.89 g (22.3 mM) of sodium hydroxide in 8.4 ml of distilled water and a solution of 5.00 g (22.2 mM) of 4-hexylbenzoyl chloride in 33.4 ml of dioxane were gradually added simultaneously at -1° to 3° C. by dropping funnels, respectively, followed by stirring for 30 minutes at 1°-2° C. After the reaction, 2.3 ml of concentrated hydrochloric acid was added to the reaction mixture to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by drying and recrystallization from ethyl acetate to obtain 4.86 g of N-(4-hexylbenzoyl)glycine (Yield: 82.9%).

Workup

  1. additionmixed
  2. additionwas added to the reaction mixture
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washwashed with water
  6. customby drying
  7. customrecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4d469e135e324d2dbd00a7fd6ebc3794
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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