Acetic Acid → HCID 21997635, compound

HRID 1977116Notes

Reaction equation

HRID 1977116 reaction equation
[C:1]([CH2:3][S:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:6]=1[NH:13][C:14](=[O:16])[CH3:15])#[N:2].OO.[OH2:19].C(O)(=[O:22])C>>[C:1]([CH2:3][S:4]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:6]=1[NH:13][C:14](=[O:16])[CH3:15])(=[O:22])=[O:19])#[N:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 21997651HCID 21997651, compound

Product 1

HCID 21997635HCID 21997635, compound

Conditions

Temperature
100 °C

Procedure

N-(2-Cyanomethylsulfanyl-4,6-difluoro-phenyl)acetamide (0.25 g) was suspended in glacial acetic acid (2 ml). Hydrogen peroxide (35%, 1 ml) was added and the mixture was stirred at 100° C. for 1 h 45 min. Then the mixture was cooled to 0° C. and water (5 ml) was added. After stirring for ½ h a white precipitate was isolated by filtration, washed with water and dried to give the title compound as white needles. Yield 0.17 g (61%); 1H-NMR (DMSO-d6), δ (ppm): 9.81 (br s, 1H, NH), 8.08-7.90 (m, 1H, Ar—H), 7.80-7.65 (m, 1H, Ar—H), 5.23 (s, 2H, CH2), 2.10 (s, 3H, CH3).

Workup

  1. temperatureThen the mixture was cooled to 0° C.
  2. stirringAfter stirring for ½ h a white precipitate
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-48bd1dbcbab84ece8ae292235ba7b5d6
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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