Chloroacetyl chloride → HCID 15580654, compound

HRID 1576931Notes

Reaction equation

HRID 1576931 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[NH:4][CH2:5][CH:6]=[O:7].C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=[O:23]>C1C=CC=CC=1>[Cl:20][CH2:21][C:22]([N:4]([CH2:5][CH:6]=[O:7])[C:3]1[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:2]=1[CH3:1])=[O:23]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 21412829HCID 21412829, compound

Product 1

HCID 15580654HCID 15580654, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The dimethyl acetal of 2-(2,6-dimethylanilino)acetaldehyde (12.2 grams; 0.058 mole), triethylamine (8.1 ml) and benzene (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The mixture was cooled in an ice bath and chloroacetyl chloride (6.6 grams; 0.058 mole) was added dropwise with stirring. After the addition was completed stirring was continued and the reaction was allowed to warm up to room temperature. After this time the mixture was filtered and the filtrate washed with dilute aqueous hydrochloric acid. The washed filtrate was dried over anhydrous magnesium sulphate and was stripped of solvent under reduced pressure to yield the desired product the dimethyl acetal of 2-[N-(α-chloroacetyl)-2,6-dimethylanilino]acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel
  3. temperatureThe mixture was cooled in an ice bath
  4. additionAfter the addition
  5. stirringwas completed stirring
  6. filtrationAfter this time the mixture was filtered
  7. washthe filtrate washed with dilute aqueous hydrochloric acid
  8. dry with materialThe washed filtrate was dried over anhydrous magnesium sulphate

Sources & evidence

ORD record
ord-3aab53a588a84fb68ab078210b4f944e
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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