Chloroacetyl chloride → HCID 12810713, compound

HRID 1704186Notes

Reaction equation

HRID 1704186 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[NH:4][CH2:5][C:6]([OH:8])=[O:7].[OH-].[Na+].[Cl:16][CH2:17][C:18](Cl)=[O:19]>C(Cl)Cl>[Cl:16][CH2:17][C:18]([N:4]([CH2:5][C:6]([OH:8])=[O:7])[C:3]1[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:2]=1[CH3:1])=[O:19]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 826274Glycine, N-(2,6-dimethylphenyl)-

Product 1

HCID 12810713HCID 12810713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

36 g (0.2 mole) of 2,6-dimethylanilinoacetic acid, 400 ml of methylene chloride and 200 ml of 1N NaOH (0.2 mole) are placed into a flask with stirrer, and 17.5 ml (0.22 mole) of chloroacetic acid chloride is slowly added dropwise with stirring, the temperature being maintained at 20°-25° by cooling with ice-water. During the dropwise addition, there is formed a white precipitate. Stirring is continued for 30 minutes and the precipitate is then filtered off with suction; the precipitate is washed with cold water, well pressed out and subsequently dried over P2O5 in a desiccator. For the purpose of obtaining further amounts of final product, the methylene chloride phase is separated in a separating funnel, dried over Na2SO4 and concentrated in vacuo, and the crystalline residue is recrystallised from ethyl acetate. There is obtained a total amount of 44 g (86% of theory) of N-chloroacetyl-2,6-dimethylanilinoacetic acid, m.p. 160° (decomposition).

Workup

  1. temperaturethe temperature being maintained at 20°-25°
  2. additionDuring the dropwise addition
  3. customthere is formed a white precipitate
  4. stirringStirring
  5. filtrationthe precipitate is then filtered off with suction
  6. washthe precipitate is washed with cold water
  7. dry with materialsubsequently dried over P2O5 in a desiccator

Sources & evidence

ORD record
ord-bc4e449b301b4031887b9e5502c77a7d
Source dataset
uspto-grants-1978_11
Patent number
US04126440

Reaction notes

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