Benzene → HCID 15580654, compound

HRID 1576938Notes

Reaction equation

HRID 1576938 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8](OC)[C:3]=1[NH:4][CH2:5][CH:6]=[O:7].[CH:14]1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:26][CH2:27][C:28](Cl)=[O:29]>O>[Cl:26][CH2:27][C:28]([N:4]([CH2:5][CH:6]=[O:7])[C:3]1[C:8]([CH3:14])=[CH:9][CH:10]=[CH:11][C:2]=1[CH3:1])=[O:29]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 21510300HCID 21510300, compound

Product 1

HCID 15580654HCID 15580654, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dipropyl acetal of 2-(2-methyl-6-methoxyanilino)acetaldehyde (15 grams), benzene (100 ml) and sodium carbonate (6.0 grams) dissolved in water (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The mixture is cooled in an ice bath and chloroacetyl chloride (6.5 grams) is added dropwise with stirring. After addition is completed stirring is continued and the reaction mixture is allowed to warm up to room temperature. After this time the mixture is filtered and the filtrate washed with dilute aqueous hydrochloric acid. The washed filtrate is dried over anhydrous magnesium sulphate and is stripped of solvent under reduced pressure to yield the desired product the dipropyl acetal of 2-[N-(α-chloroacetyl)-2,6-dimethylanilino]acetaldehyde.

Workup

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

Sources & evidence

ORD record
ord-35e591e00b3f4c21b70dfc55e3141944
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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