Toluene → 2-Chloro-2'-methoxy-5'-methylacetanilide

HRID 35323

Reaction equation

HRID 35323 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[NH2:10].CC1C=CC=CC=1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>O>[Cl:18][CH2:19][C:20]([NH:10][C:4]1[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:21]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6577Chloroacetyl chlorideHCID 84452-Methoxy-5-Methylaniline

Product 1

HCID 7369912-Chloro-2'-methoxy-5'-methylacetanilideYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 49.2 parts of 2-methoxy-5-methylbenzenamine and 270 parts of methylbenzene were added dropwise 22.5 parts of 2-chloroacetyl chloride while cooling (ice-bath) at 10°-20° C. Upon completion, stirring was continued for 1.50 hours at room temperature. 200 Parts of water were added. The organic phase was separated, washed with water, dried, filtered and evaporated. The oily residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 28.2 parts (66%) of 2-chloro-N-(2-methoxy-5-methylphenyl)acetamide; mp. 83.9° C. (intermediate 66).

Workup

  1. temperaturewhile cooling (ice-bath) at 10°-20° C
  2. customThe organic phase was separated
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue was crystallized from 2,2'-oxybispropane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-fc76ba613db148e5b72e5a3ba33e1cb9
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Linked notes

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