Benzene → HCID 86735046, compound

HRID 1658968Notes

Reaction equation

HRID 1658968 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:3]=1[NH:4][CH2:5][CH:6]=[O:7].C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1.[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[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:2]=1[CH3:1])=[O:29]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 21412834HCID 21412834, compound

Product 1

HCID 86735046HCID 86735046, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 2-(2-methyl-5-cyanoanilino)-acetaldhyde (0.1 mole), sodium carbonate (0.06 mole) dissolved in water (50 ml) and benzene (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and cooling means. The mixture is cooled to a temperature of about 0°C and α-chloroacetyl chloride (0.11 mole) is incrementally added with stirring. After the addition is completed stirring is continued and the reaction mixture is permitted to warm to room temperature. After this time the mixture is filtered, washed with dilute hydrochloric acid and stripped of solvent to yield the desired product the dimethyl acetal of 2-(N-α-chloroacetyl-2-methyl-5-cyanoanilino)acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and cooling means
  3. additionis incrementally added
  4. additionAfter the addition
  5. stirringis completed stirring
  6. filtrationAfter this time the mixture is filtered
  7. washwashed with dilute hydrochloric acid

Sources & evidence

ORD record
ord-657fd76ef95b49fa97b4be4221211154
Source dataset
uspto-grants-1976_06
Patent number
US03966811

Reaction notes

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