Benzene → HCID 15580654, compound

HRID 1576933Notes

Reaction equation

HRID 1576933 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].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:25][CH2:26][C:27](Cl)=[O:28]>O>[Cl:25][CH2:26][C:27]([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:28]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 21412829HCID 21412829, compound

Product 1

HCID 15580654HCID 15580654, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The diethyl acetal of 2-(2,6-dimethylanilino)acetaldehyde (13 grams), benzene (50 ml) and sodium carbonate (5.8 grams) dissolved in water (50 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 (6.2 grams) was added dropwise with stirring. After addition was completed stirring was continued and the reaction mixture 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 diethyl acetal of 2-[N-(α-chloroacetyl)-2,6-dimethylanilino]acetaldehyde.

Workup

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

Sources & evidence

ORD record
ord-596014bab18a4488877c7110f87bc763
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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