Sulfuric Acid → HCID 59564946, compound

HRID 1259315Notes

Reaction equation

HRID 1259315 reaction equation
S(=O)(=O)(O)O.O=[C:7]([CH3:25])[CH2:8][NH:9][C:10](=[O:24])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)=[O:12]>O>[CH3:25][C:7]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:11](=[O:12])[C:10](=[O:24])[NH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59564945HCID 59564945, compound

Product 1

HCID 59564946HCID 59564946, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Conc. sulphuric acid (2.35 L) was heated to 50-55° C. and N-(2-oxopropyl)-N′-[3-(trifluoromethyl)phenyl]ethanediamide (200 g, 1 eq)) was then added portion-wise over 2 hours to give a clear brown solution. After 3.25 hours the reaction was cooled to 20° C. The reaction mixture was then added to water (6 L), keeping the temperature below 10° C. The white slurry was then stirred at 0-5° C. for a further 1 hour before filtering. The filter cake was washed with water (2 L) and the damp product recharged to the flask. Water (0.85 L) was charged and the mixture stirred for 30 minutes. The mixture was filtered and the filter cake washed with water (0.25 L). The title compound was isolated as a water-wet, off-white solid (228.0 g, water content=26.5%, corrected mass 168.0 g, 90%).

Workup

  1. customto give a clear brown solution
  2. customthe temperature below 10° C
  3. filtrationbefore filtering
  4. washThe filter cake was washed with water (2 L)
  5. additionWater (0.85 L) was charged
  6. stirringthe mixture stirred for 30 minutes
  7. filtrationThe mixture was filtered
  8. washthe filter cake washed with water (0.25 L)

Sources & evidence

ORD record
ord-dde67dd508834a928b395882fda6a1b2
Source dataset
uspto-grants-2013_06
Patent number
US08466284B2

Reaction notes

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