Benzene → HCID 15580654, compound

HRID 2071199Notes

Reaction equation

HRID 2071199 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(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1.[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

Conditions

Temperature
0 °C

Procedure

The diethyl acetal of 2-(2,6-dimethylanilino)-acetaldehyde (13.0 grams), sodium carbonate (5.8 grams) dissolved in water (50 ml) and benzene (50 ml) were charged into a reaction vessel equipped with a mechanical stirrer, thermometer and cooling means. The mixture was cooled to about 0° C. and chloroacetyl chloride (6.2 grams) was incrementally added with stirring. After the addition was complete stirring was continued and the reaction mixture was permitted to warm to room temperature. After this time the mixture was filtered, washed with dilute hydrochloric acid and 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. customequipped with a mechanical stirrer
  2. temperaturethermometer and cooling means
  3. additionAfter the addition
  4. stirringwas complete stirring
  5. temperatureto warm to room temperature
  6. filtrationAfter this time the mixture was filtered
  7. washwashed with dilute hydrochloric acid

Sources & evidence

ORD record
ord-b5a958172c9b441b856c9dbf72cbd07b
Source dataset
uspto-grants-1977_09
Patent number
US04046554

Reaction notes

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