Sulfuric Acid → 3,5-Dichloro-4-[(2-chloroacetyl)amino]benzamide

HRID 35325Notes

Reaction equation

HRID 35325 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][CH2:7][C:8]([NH:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:12]=1[Cl:20])=[O:9]>>[Cl:20][C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([Cl:17])[C:11]=1[NH:10][C:8](=[O:9])[CH2:7][Cl:6])[C:18]([NH2:19])=[O:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 147225642-chloro-N-(2,6-dichloro-4-cyanophenyl)acetamide

Product 1

HCID 142302773,5-Dichloro-4-[(2-chloroacetyl)amino]benzamide

Conditions

Temperature
0 °C

Procedure

16.8 Parts of concentrated sulfuric acid were stirred and cooled to 0° C. and there were added portionwise 4.2 parts of 2-chloro-N-(2,6-dichloro-4-cyanophenyl)acetamide. Upon completion, stirring was continued for 3 hours in an ice-bath. The reaction mixture was allowed to stand overnight at room temperature and poured onto ice-water. The precipitated product was filtered off, washed with water, dried and boiled in acetonitrile. The product was filtered off and dried, yielding 2.7 parts of 3,5-dichloro-4-[(2-chloroacetyl)amino]benzamide; mp. +260° C. (intermediate 71).

Workup

  1. waitto stand overnight at room temperature
  2. additionpoured onto ice-water
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. customdried
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-2e64d416150e46e9a75abb32f91caa70
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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