Chloroacetyl chloride → HCID 14722531, compound

HRID 1073177Notes

Reaction equation

HRID 1073177 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:16])[C:3]=1[NH2:17].[Cl:18][CH2:19][C:20](Cl)=[O:21]>CC1C=CC=CC=1>[Cl:18][CH2:19][C:20]([NH:17][C:3]1[C:4]([CH3:16])=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][C:2]=1[CH3:1])=[O:21]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 133699574-Benzyloxy-2,6-dimethylaniline

Product 1

HCID 14722531HCID 14722531, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 20 parts of 2,6-dimethyl-4-(phenylmethoxy)benzenamine and 270 parts of methylbenzene were added portionwise 10.9 parts of 2-chloroacetyl chloride (exothermic reaction, the temperature rose to 30° C.). Upon complete addition, the reaction mixture was stirred for 1 hour at reflux temperature. After cooling, the precipitated product was filtered off and dried, yielding 23.8 parts (89%) of 2-chloro-N-[2,6-dimethyl-4-(phenylmethoxy)phenyl]acetamide; mp. 165.3° C. (int. 71).

Workup

  1. customexothermic reaction
  2. customrose to 30° C.
  3. additionUpon complete addition
  4. temperatureat reflux temperature
  5. temperatureAfter cooling
  6. filtrationthe precipitated product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-e7f14e7c7c93488d9e1fb3fd0703397d
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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