Chloroacetyl chloride → Diethatyl-ethyl

HRID 1995033Notes

Reaction equation

HRID 1995033 reaction equation
[CH2:1]([C:3]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH3:17])[C:4]=1[NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[Cl:18][CH2:19][C:20](Cl)=[O:21].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:18][CH2:19][C:20]([N:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]1[C:12]([CH2:16][CH3:17])=[CH:13][CH:14]=[CH:15][C:3]=1[CH2:1][CH3:2])=[O:21]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 170107Glycine, N-(2,6-diethylphenyl)-, ethyl ester

Product 1

HCID 38090Diethatyl-ethyl

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

23.5 Grams (0.1 mol) of ethyl 2,6-diethylanilinoacetate and 11.3 g (0.1 mol) of monochloroacetic acid chloride were dissolved in 100 ml of benzene, 11.0 g of triethylamine was then added dropwise thereto with stirring maintaining the reaction temperature at 10°-20° C. and, thereafter, stirring was continued for further 2 hours at a room temperature. The reaction solution was washed with successive, 5% sodium hydroxide aqueous solution, 5% hydrochloric acid aqueous solution, and water. Then, the benzene layer was dried over anhydrous sodium sulfate. Thereafter, benzene was removed under reduced pressure to obtain the end product, ethyl N-chloroacetyl-2,6-diethylanilinoacetate. nD26 : 1.5225.

Workup

  1. temperaturemaintaining the reaction temperature at 10°-20° C.
  2. stirringstirring
  3. washThe reaction solution was washed with successive, 5% sodium hydroxide aqueous solution, 5% hydrochloric acid aqueous solution, and water
  4. dry with materialThen, the benzene layer was dried over anhydrous sodium sulfate
  5. customThereafter, benzene was removed under reduced pressure

Sources & evidence

ORD record
ord-a0f3126b77a3454eb572a0aa4bee66dd
Source dataset
uspto-grants-1983_09
Patent number
US04402734

Reaction notes

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