Chloroacetyl chloride → 2-Chloro-N-(2,6-dichlorophenyl)-N-(4-methoxyphenyl)acetamide

HRID 467287Notes

Reaction equation

HRID 467287 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[CH:5][CH:4]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=1[N:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:20](=[O:21])[CH2:19][Cl:18]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 156786462,6-Dichloro-N-(4-methoxyphenyl)aniline

Product 1

HCID 156786472-Chloro-N-(2,6-dichlorophenyl)-N-(4-methoxyphenyl)acetamideYield 64%

Procedure

Under anhydrous conditions, a mixture of N-(4-methoxyphenyl)-2,6-dichloroaniline (20.2 g, 75.4 mmmol) in 175 mL of chloroacetyl chloride is heated at reflux for 1 hour. The excess acid chloride is evaporated in vacuo and the residue partitioned between saturated NaHCO3 solution and ethyl acetate (30 mL each). The organic phase is washed with brine (30 mL) and dried (Na2SO4). Removal of solvent affords an amber oil. Crystallization of the crude oil from methanol affords the title product (16.63 g, 64%, white needles, m.p. 105°-106° C., lit: 127°-128° C. from methanol) as a 1:1 mixture of rotamers.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. customThe excess acid chloride is evaporated in vacuo
  4. customthe residue partitioned between saturated NaHCO3 solution and ethyl acetate (30 mL each)
  5. washThe organic phase is washed with brine (30 mL)
  6. dry with materialdried (Na2SO4)
  7. customRemoval of solvent
  8. customaffords an amber oil
  9. customCrystallization of the crude oil from methanol

Sources & evidence

ORD record
ord-ff26435721274aefbe4d0c975d3deafd
Source dataset
uspto-grants-1992_10
Patent number
US05159085

Reaction notes

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