Acetic Anhydride → HCID 20514654, compound

HRID 1902664Notes

Reaction equation

HRID 1902664 reaction equation
[CH:1]1([CH:7]([C:11](=[S:21](=[O:23])=[O:22])[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])[C:8](O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>>[C:15]1([N:14]2[C:12](=[O:13])[C:11](=[S:21](=[O:23])=[O:22])[CH:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]2=[O:9])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 20514656HCID 20514656, compound

Product 1

HCID 20514654HCID 20514654, compoundYield 86%

Procedure

3.39 g. (0.01 mole) of 2-cyclohexyl-sulfonyl-4-phenylamino-4-oxo-butanoic acid are dissolved in 20 ml. of acetic acid anhydride and 0.82 g. (0.01 mole) anhydrous sodium acetate and the solution is heated for 1 hour at 100° C. The reaction mixture is then poured on crushed ice and the precipitated compound named filtered off and washed with water in order to remove acid. 2.76 g. (86%) of the named compound are obtained. M.p.: 149°-151° C. After recrystallization from methanol m.p.: 150°-152° C. Minimal inhibitory concentration inhibiting the growth of Trychophyton mentagrophytes: 2.5 μg/ml. and of Epidermophyton floccosum: 1.0 μg./ml.

Workup

  1. additionThe reaction mixture is then poured
  2. customon crushed ice
  3. filtrationthe precipitated compound named filtered off
  4. washwashed with water in order
  5. customto remove acid

Sources & evidence

ORD record
ord-c21c885e7dfb45029b8a28ce1c66bcd7
Source dataset
uspto-grants-1982_12
Patent number
US04364958

Reaction notes

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