Sulfuric Acid → HCID 15087739, compound

HRID 1494650Notes

Reaction equation

HRID 1494650 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[CH2:14][Cl:15])(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:18]>>[C:1]([C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[CH2:14][Cl:15])[C:10]([NH2:11])=[O:18])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 15087740HCID 15087740, compound

Product 1

HCID 15087739HCID 15087739, compoundYield 61.6%

Procedure

15.7 Parts of N-(2-acetyl-4-cyanophenyl)-2-chloroacetamide were added portionwise to 146.4 parts of concentrated sulfuric acid at room temperature. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was poured into 500 parts of crushed ice while stirring. The precipitated product was filtered off and suspended in water. The precipitated product was filtered off, washed with water and suspended in 20 parts of acetonitrile. The product was filtered off, boiled in 20 parts of acetonitrile and filtered off, after cooling, yielding 10.4 parts (61.6%) of 3-acetyl-4-[(2-chloroacetyl)amino]benzamide (int. 114).

Workup

  1. additionUpon complete addition
  2. additionThe reaction mixture was poured into 500 parts of crushed ice
  3. stirringwhile stirring
  4. filtrationThe precipitated product was filtered off
  5. filtrationThe precipitated product was filtered off
  6. washwashed with water
  7. filtrationThe product was filtered off
  8. filtrationfiltered off
  9. temperatureafter cooling

Sources & evidence

ORD record
ord-fafc2ace3e624672a4773e6551aaf6d0
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

Loading…