Chloroacetyl chloride → HCID 20488927, compound

HRID 1995034Notes

Reaction equation

HRID 1995034 reaction equation
[CH2:1]([C:3]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH3:18])[C:4]=1[NH:5][CH2:6][C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[CH3:2].[Cl:19][CH2:20][C:21](Cl)=[O:22].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:19][CH2:20][C:21]([N:5]([CH2:6][C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[C:4]1[C:13]([CH2:17][CH3:18])=[CH:14][CH:15]=[CH:16][C:3]=1[CH2:1][CH3:2])=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 20488950HCID 20488950, compound

Product 1

HCID 20488927HCID 20488927, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

24.7 Grams of allyl 2,6-diethylanilinoacetate and 11.3 g 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, allyl N-chloroacetyl-2,6-diethylanilinoacetate. nD21.5 : 1.5288.

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-999ca39a31474e7fbdb948651ae0e44d
Source dataset
uspto-grants-1983_09
Patent number
US04402734

Reaction notes

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