Acetic Acid → HCID 178466866, compound

HRID 1082001Notes

Reaction equation

HRID 1082001 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:17]([C:19]2[CH:20]=[N:21][N:22]([CH2:25][CH3:26])[C:23]=2[OH:24])=[O:18])[C:5]([CH3:16])=[C:6]2[C:11]=1[S:10][CH:9]([CH3:12])[CH2:8][CH:7]2[O:13][CH2:14][CH3:15].C(O)(=[O:29])C.OO.[OH2:33]>>[F:1][C:2]1[CH:3]=[C:4]([C:17]([C:19]2[CH:20]=[N:21][N:22]([CH2:25][CH3:26])[C:23]=2[OH:24])=[O:18])[C:5]([CH3:16])=[C:6]2[C:11]=1[S:10](=[O:29])(=[O:33])[CH:9]([CH3:12])[CH2:8][CH:7]2[O:13][CH2:14][CH3:15]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 178466848HCID 178466848, compound2×

Product 1

HCID 178466866HCID 178466866, compound

Conditions

Temperature
100 °C

Procedure

A 50-ml egg-plant type flask was charged with 4.8 g (0.013 mol) of 8-fluoro-4-ethoxy-2,5-dimethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman (Compound 43), 20 ml of acetic acid and 4.5 g (0.04 mol) of a 30% hydrogen peroxide aqueous solution, and the mixture was heated at 100° C. for 1 hour. After allowed to cool, the reaction mixture was poured into 100 ml of water. The precipitated oil was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 4.6 g of 8-fluoro-4-ethoxy-2,5-dimethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonyl-thiochroman-1,1-dioxide (Compound 59) shown in Table 5.

Workup

  1. temperatureto cool
  2. extractionThe precipitated oil was extracted with ethyl acetate
  3. dry with materialthe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76fcf5117f4448efbf0353ba9c0cf785
Source dataset
uspto-grants-1996_12
Patent number
US05587484

Reaction notes

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