Acetic Acid → HCID 22277834, compound

HRID 1064007Notes

Reaction equation

HRID 1064007 reaction equation
[C:1]([C:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[S:8][C:7]=2[CH:6]=[CH:5][C:4]=1[NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])#[N:2].C(O)(=[O:25])C.OO.[OH2:29]>>[C:1]([C:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[S:8](=[O:25])(=[O:29])[C:7]=2[CH:6]=[CH:5][C:4]=1[NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])#[N:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 22277814HCID 22277814, compound

Product 1

HCID 22277834HCID 22277834, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 1-cyano-2-pivaloylaminodibenzothiophene (Example 68; 0.034 g, 0.11 mmol) glacial acetic acid (2 ml) and 30% hydrogen peroxide (0.2 ml) was heated at 80° C. for 4 hours. The mixture was cooled and poured into water. The precipitate was filtered and washed extensively with water to give the title compound. NMR 9.95 (s, 1H), 8.57 (d, 1H), 8.32 (d, 1H), 8.11 (d, 1H), 7.95 (t, 1H), 7.82 (t, 1H), 7.75 (d, 1H), 1.28 (s, 9H); m/z 341.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe precipitate was filtered
  3. washwashed extensively with water

Sources & evidence

ORD record
ord-cdc3f352675d442b87440a92efd5bb32
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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