Benzene → HCID 21510285, compound

HRID 1576936Notes

Reaction equation

HRID 1576936 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH3:14])[C:4]=1[NH:5][CH2:6][CH:7]=[O:8])[CH3:2].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:27][CH2:28][C:29](Cl)=[O:30]>O>[Cl:27][CH2:28][C:29]([N:5]([CH2:6][CH:7]=[O:8])[C:4]1[C:9]([CH2:13][CH3:14])=[CH:10][CH:11]=[CH:12][C:3]=1[CH2:1][CH3:2])=[O:30]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 214128262-(2,6-Diethylanilino)acetaldehyde

Product 1

HCID 21510285HCID 21510285, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dimethyl acetal of 2-(2,6-diethylanilino)acetaldehyde (13 grams), benzene (75 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 dimethyl acetal of 2-[N-(α-chloroacetyl)-2,6-diethylanilino]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-d59bfad340734446a14733926ddaaf97
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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