Acetic Acid → HCID 21997642, compound

HRID 1977119Notes

Reaction equation

HRID 1977119 reaction equation
[C:1]([CH2:3][S:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[NH:12][C:13](=[O:15])[CH3:14])#[N:2].OO.[OH2:18].C(O)(=[O:21])C>>[C:1]([CH2:3][S:4]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[NH:12][C:13](=[O:15])[CH3:14])(=[O:21])=[O:18])#[N:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 21997644HCID 21997644, compound

Product 1

HCID 21997642HCID 21997642, compound

Conditions

Temperature
100 °C

Procedure

N-(2-Cyanomethylsulfanyl-4-fluoro-phenyl)acetamide (0.43 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. Then the mixture was cooled to 0° C. and water (15 ml) was added. After stirring for 10 min a white precipitate was isolated by filtration, washed with water and dried. Recrystallization from 96% ethanol afforded the title compound as white needles, mp 154-157° C.; yield 0.28 g (58%); 1H-NMR (DMSO-d6), δ (ppm): 9.64 (s, 1H, NH), 7.99-7.64 (m, 3H, Ar—H), 5.30 (s, 2H, CH2), 2.08 (s, 3H, CH3).

Workup

  1. temperatureThen the mixture was cooled to 0° C.
  2. stirringAfter stirring for 10 min a white precipitate
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried
  6. customRecrystallization from 96% ethanol

Sources & evidence

ORD record
ord-b25361d00ce14d448e088d3537b8928f
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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