Sulfuric Acid → 1312454-85-5

HRID 1619328Notes

Reaction equation

HRID 1619328 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])/[CH:11]=N/O)[CH:5]=[C:6]([F:8])[CH:7]=1.[OH:15]S(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11](=[O:15])[C:10](=[O:14])[NH:9]2)=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 87327711HCID 87327711, compound

Product 1

HCID 672585381312454-85-5

Conditions

Temperature
90 °C

Procedure

(E)-N-(3-bromo-5-fluorophenyl)-2-(hydroxyimino)acetamide (6.13 g, 23.6 mmol) was slowly added to a solution of conc. H2SO4 (30 mL) in an ice bath. The temperature of the reaction mixture was maintained below 50° C. After completion of the addition, the solution was heated to 90° C. for 1 h. After it was cooled to rt, the mixture was poured into ice-water and stirred vigorously for 1 h. The insoluble solid was filtered and washed with water, dried under vacuum to provide 7.4 g of crude product, which was used into the next step without further purification. MS (ESI): 242, 244 (MH−).

Workup

  1. temperatureThe temperature of the reaction mixture was maintained below 50° C
  2. additionAfter completion of the addition
  3. temperatureAfter it was cooled to rt
  4. filtrationThe insoluble solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-f1dc82d4ff814c8d979a94c482203825
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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